Abstract
A review covering some of the key catalytic transformations of the major monoterpene feedstocks. Monoterpenes are key ingredients in the flavor and fragrance industry, with α- and β-pinene (obtained from turpentine) being some of the most important. The review focuses on the hydrocarbons; pinene, limonene, carene, and the interconversion of the monooxygenates; geraniol/nerol, citronellol, citral, and citronellal. The major areas covered are catalytic hydrogenation/hydrogenolysis, dehydrogenation, rearrangement/isomerization/aromatization, reactions with carbon monoxide, epoxidation, and the addition of alcohols and acids.
Similar content being viewed by others
References
V. Ipat'ev and G.J. Balachinskii, Russ. Phys. Chem. Soc. 43 (1912) 1754; V. Ipat'ev, Ber. 43 (1911) 3546.
E.P. Armstrong and T.P. Hilditch, Proc. R. Soc. London 108A (1925) 121.
E. Sakmoiraghi and O. Grassi, Giorn. Chim. Ind. Applicata 13 (1931) 480.
G. Dupont and V. Desreux, Compt. Rend. 203 (1936) 733.
H.A. Smith, J.F. Fuzek and H.T. Meriwether, J. Am. Chem. Soc. 71 (1949) 3765.
H.A. Smith, J.F. Fuzek and F. John, J. Am. Chem. Soc. 72 (1950) 3454.
P. Le Maux, G. Sigmonneaux, J. Organomet. Chem. 229(2) (1982) C24.
V. Ipat'ev, F.J. Paulik, H. Pines, J. Am. Chem. Soc. 75 (1953) 3179.
G.N. Lukina, O.A. Tyurenkova, Alma-Ata (1963) volume date (1962) 445.
C. Allaandrieu, G. Descotes, J.P. Praly, J. Sabadie, Bull. Soc. Chim. Fr. 5–6 (1977) 519.
S. Xiao, H. Xing, L. Gu, Lirchan Huaxae Yu Gongye 1 (1981) 13.
T. Jenke and G. Suess-Fink, J. Organomet. Chem. 405 (1991) 383.
S.H. Ko and T.C. Chou, Ind. Eng. Chem. Res. 32 (1993) 1579. (b) S.H. Ko and T.C. Chou, Can. J. Chem. Eng. 72 (1994) 862. (c) S.H. Ko and T.C. Chou, J. Chin. Inst. Chem. Eng. 25 (1994) 155. (d) S.H. Ko and T.C. Chou, Ind. Eng. Chem. Res. 34 (1995) 457.
A.B. Tereshko, L.I. Basalaeva, N.G. Kozlov and V.A. Tarasevich, Zh. Org. Khim. 32 (1996) 823.
WO9744304 To: Nigu Chemie Gmbh, Germany.
J. Ricardo, P.D. Grau, C.G. Zgolicz, A.T. Hugo, J. Mol. Catal. A: Chem. 148 (1999) 203.
To SCM Corporation U.S. 4,018,842.
WO2002072508 To: Valtion Teknillinen Tutkimuskeskus, Finland.
C.A. Brown and H.C. Brown, J. Am. Chem. Soc. 84 (1962) 2829. (b) W. Cocker, et al. J. Chem. Soc. C. 41 (1966) (c) Lipp, Chem. Ber. 63 (1930) 411. (d) C. Larpent, R. Dabard and H. Patin, Tetrahedron Lett. 28 (1987) 2507.
Faucounau and C.R. Hebd. Seances Acad. Sci. 203 (1936) 406. (b) A.A. Pavia, P. Geneste and J.-L. Olive, Bull. Soc. Chim. Fr. 2 (1981) 24. (c) L.M. Jackman, R.L. Webb and H.C. Yick, J. Org. Chem. 47 (1982). (d) D.C. Tabor, F.H. White, L.W. Collier and S.A. Evans, J. Org. Chem. 48(10) (1983) 1638. (e) A. Fischli, P.M. Mueller, Helv. Chim. Acta. 63 (1980) 1619. (f ) G. Jeske, H. Lauke, H. Mauermann, H. Schumann and T.J. Marks, J. Am. Chem. Soc. 107 (1985) 8111. (g) J.O. Osby, S.W. Heinzman and B. Ganem, J. Am. Chem. Soc. 108 (1986) 67. (h) T. Kitahara, M. Mori and K. Mori, Tetrahedron 43 (1987) 2689. (i) J. Wright, G.J. Drtina, R.A. Roberts and L.A. Paquette, J. Am. Chem. Soc. 110 (1988) 5806. ( j) F. Scott, H.G. Raubenheimer, G. Pretorius and A.M. Hamese, J. Organomet. Chem. 384 (1990) C17–C20. k) D.S. Shephard, T. Maschmeyer, G. Sankar, J.M. Thomas and D. Ozkaya, Chem. Eur. J. 4 (1998) 1214.
Escourrou, Bull. Soc. Chim. Fr. 43 (1928) 1207. (b) Adams and Garvey, J. Am. Chem. Soc. 48 (1926) 481.
Escourrou, Bull. Soc. Chim. Fr. 43 (1928) 1210. (b) Dupont, Dereux and Dulou, Bull. Soc. Chim. Fr. 4 (1937) 2018. (c) T. Ishimura, Bull. Chem. Soc. Jpn. 18 (1943) 194. (d) Grignard and Escourrou, Bull. Soc. Chim. Fr. 37 (1925) 546.
Escourrou, Bull. Soc. Chim. Fr. 43 (1928) 1204.
Houlihan, J. Org. Chem. 23 (1958) 689.
B.B.C. Ranu and A. Sarkar, Tetrahedron Lett. 35 (1994) 8649.
M. Kikuchi, Kogyo Kagaku Zasshi 65 (1962) 1239. (b) M. Kikuchi, Kogyo Kagaku Zasshi 66 (1963) 464. (c) M. Kikuchi, Kogyo Kagaku Zasshi 66 (1963) 461.
D.V. Sokol'skii, A.M. Pak, S.M. Turganbaeva, S.R. Konuspaer and M.A. Ginzburg, J. Appl. Chem. USSR 54 (1981) 1345. (b) J. Court, F. Janati-Idrissi, S. Vidal and P. Wierzchowski, J. Chim. Phys. Phys. Chim. Biol. 87 (1990) 379.
Singh, K. Utpal, M.N. Sysak and M.A. Vannice, J. Catal. 191 (2000) 165.
K. Utpal, Singh and M. Vannice, J. Catal. (2000) 181.
S.-I. Inoue, M. Osada, K. Koyano, H. Takaya and R. Noyori, Chem. Lett. (1985) 1007. (b) H. Takaya, T. Ohta, N. Sayo, H. Kumobayashi and S. Akutagawa, J. Am. Chem. Soc. 109 (1987) 1596. (c) K. Mashima, K. Kuzushi, Koh-hei, T. Ohta, R. Noyori and H. Takaya, J. Chem. Soc., Chem. Commun. (1989) 1208. (d) K. Mashima, Kusano, Koh-hei, N. Sato, Y.-I. Matsumura and K. Nozaki, J. Org. Chem. 59 (1994) 3064. (e) Y. Sun, R.N. Landau, J. Wang, C. LeBlond and D.G. Blackmond, J. Am. Chem. Soc. 118 (1996) 1348. (f )Y. Sun, C. LeBlond, J. Wang, D.G. Blackmond, J. Laquidara and J.R. Sowa, J. Am. Chem. Soc. 117 (1995) 12647. (g) Y. Sun, J. Wang, C. LeBlond, R.A. Reamer and J. Laquidara, J. Organomet. Chem. 548(1) (1997) 65.
X. Zhang, K. Mashine, K. Koyano, N. Sayo, H. Kumobayashi, S. Akutagawa and H. Takaya, J. Chem. Soc., Perkin Trans. 1 16 (1994) 2309.
B. Heiser, E.A. Broger and Y. Crameri, Tetrahedron: Asymmetry 2 (1991) 51. (b) M.A. Ali, S. Allaoud, A. Karim, A. Roucoux and A. Mortreux, Tetrahedron: Asymmetry 6 (1995) 369. (c) T. Benincon, E. Brenna, F. Sannicolo, L. Trimarco and P. Antognazza, J. Org. Chem. 61 (1996) 6244. (d) T. Benincon, E. Cesarotti, O. Piccolo and F. Sannicolo, J. Org. Chem. 65(7) (2000) 2043.
G. Righi and L. Rosii, Synth. Commun. 26 (1996) 1321.
L. Cerveny and V. Ruzicka, Seifen Oele Fette Wachse 114 (1988) 605.
R.P. Linstead, K.O.A. Michaelis and S.L.S. Thomas, J. Chem. Soc. (1949) 1139.
T. Chaudron and R. Pallaud, Compt. Rend. 253 (1961) 140.
L.M. Yeddanapalli and P. desikan, J. Sci. Ind. Res. B21 (1962) 116–123.
P. Ratnasamy, V. Krishnasamy and L.M. Yeddanapalli, Indian J. Chem. 9 (1971) 131.
S.C. Kohli, H. Veeramani and M.G. Rao, Indian J. Technol. 11 (1973) 308.
V. Krishnasamy and L.M. Yeddanapalli, Can. J. Chem. 55 (1977) 3046.
V. Krishnasamy, Aust. J. Chem. 33 (1980) 1313.
Y. Fujihara, C. Hata, Y. Matsubara and Yukagaku, 25 (1975) 314. (b) Y. Fujihara, C. Hata, Y. Matsubara and Yukagaku, 24 (1975) 654.
Y. Saito and Y. Ogino, Nippon Kagaku Kaishi 6 (1976) 1018.
To Rhodia Inc. U.S. 3,971,830.
M. Hayashi, K.N. Yamada and Shu-zo, J. Chem. Soc., Perkin Trans. 1 10 (2000) 1500.
D.V. Banthorpe and D. Whittaker, Quart. Rev. 20 (1966) 373.
J.-L. Li, B. Li, X.-T. Xu and C.-Q. Wei, Guangxi Huagong 28 (1999) 23.
G.A. Rudakov and M.M. Shestaeva, J. Chem. Chem. USSR 25 (1955) 597.
G.A. Rudakov and M.M. Shestaeva, Zhur. Obshchel Khim. 26 (1956) 2357.
A.F. Plate and E.M. Mil'vitskaya, Teknologiya 10 (1967) 1340.
R. Ohnishi and k. Tanabe, Chem. Lett. 3 (1974) 207.
All to SCM Corp., USA. NL-7403890, U.S. 3,974,102, U.S. 3,974,103, U.S. 4,000,207, U.S. 4,000,208.
J. Ouyang, C. Sheng, Y. Ding, Y. Wang and C. Cui, Huagong Keji 7(1) (1999) 18.
K.A.D. Swift, in Fine Chemicals through Heterogeneous Catalysis, R.A. Sheldon and H. van Bekkum (eds) (Wiley-VCH, 2001) p. 242.
N.F. Sulakhutdinov and V.A. Barkhash, Chem. Nat. Compd 37 (2001) 495.
L.P. Petelina, M.I. Goryaev and K.D. Dzhandosova, Izv. Akad. Nauk Kaz. SSR, Ser. Khimi. 17 (1967) 93.
Sh.-B. Battalova and T.R. Mukitanova, Izv. Akad. Nauk Kaz. SSR, Ser. Khim. 25 (1975) 49. (b) Sh.-B. Battalova, T.R. Mukitanova and R.D. Dzhakisheva, Izv. Akad. Nauk Kaz. SSR, Ser. Khimi. 27 (1977) 71. (c) Sh.-B. Battalova and T.R. Mukitanova, Vestn. Akad. Nauk Kaz. SSR, Ser. Khimi. 7 (1979) 41. (d) Sh.-B. Battalova, T.R. Mukitanova, N.D. Pak and R.N. Dzhakisheva, Izv. Akad. Nauk Kaz. SSR, Ser. Khimi. 3 (1979) 46.
Sh.-B. Battalova, A.A. Likerova and T.R. Mukitanova, Izv. Akad. Nauk Kaz. SSR, Ser. Khim. 25 (1975) 70.
Sh.-B. Battalova and T.R. Mukitanova, Gidroliz. Lesokhim. Prom. 2 (1984) 8. (b) Sh.-B. Battalova, T.R. Mukitanova and Kh.-G. Tabanova, Vestn. Akad. Nauk Kaz. SSR, Ser. Khim. 10 (1990) 52.
G.A. Rudakov, T.N. Pisareva and N.F. Ovsyukova, Gidroliz. Lesokhim. Prom. 6 (1981) 14.
A. Severino, J. Vital and L.S. Lobo, Stud. Surf. Sci. Catal. 78 (1993) 685. (Heterogeneous Catalysis & Fine Chemicals III).
O. Masini, L.M. Grzona, N.A. Carnelli, R.R. Montenegro, A.L. Carrascull and M.I. Ponzi, Inf. Tecnol. 8 (1997) 163.
S. Findik and G. Guenduez, J. Am. Oil Chem. Soc. 74 (1997) 1145.
A.I. Allahuerdiev, S. Irandoust and D.Y. Murzin, J. Catal. 185 (1999) 352.
F.D. Ovcharenko and I. Dimov, Dokl. Bolg. Akad. Nauk. 34 (1981) 533. (b) F.D. Ovcharenko, I. Dimov and Y.I. Tarasevich, Ukr. Khim. Zh. 49 (1983) 24.
V. Krishnasamy and P. Ratnasamy, J. Indian Chem. Soc. 59 (1982) 1151.
C. Breen, Appl. Clay Sci. 15 (1999) 187.
Q. Yang, J. Qi, J. Cao and L. Luo, Huaxue Yanjiu yu Yingyong 9 (1997) 250.
X.-T. Xu, L.J.-L. Bin and C.-Q. Wei, Guangxi Huagong 29(7–8) (2000) 15.
Sabatier, C.R. Gaudion, Hebd. Seances Acad. Sci. 168 (1919) 671.
Venable, J. Am. Chem. Soc. 45 (1923) 728.
N.D. Zelinsky and R.Y. Lewina, Chem. Ber. 62 (1929) 339.
R.P. Linstead, K.O.A. Michaelis and S.L.S. Thomas, J. Chem. Soc. (1940) 1139. (b) H. Pines, R.C. Olberg and V.N. Ipatieff, J. Am. Chem. Soc. 70 (1948) 533. (c) N.D. Zelinsky and R.Y. Lewina, Justus Liebigs Ann. Chem. 476 (1929) 65.
U.S. 2,741,645 To: Glidden Co.
M. Kikuchi, Kogyo Kagaku Zasshi 64 (1961) 334.
A. Stanislaus and L.M. Yeddanapalli, Can. J. Chem. 50 (1972) 113.
P. Mathur, V. Krishnasamy and K. Chandrasekharan, J. Indian Chem. Soc. 59 (1982) 970. (b) V. Krishnasamy and P. Mathur, Curr. Sci. 52 (1983) 624.
V. Krishnasamy, P. Mathur and K. Balasubramian, Chem. Eng. Commun. 23 (1983) 115.
V. Krishnasamy, P. Mathur and K. Chandrasekharan, J. Indian Chem. Soc. 60 (1983) 49.
V. Krishnasamy and V. Mohan, J. Indian Chem. Soc. 60 (1983) 359.
D.M. Roberge, D. Buhl, J.P.M. Niederer and W.F. Holderich, Appl. Catal. A: Gen. 215 (2001) 111.
To Arizona Chemical Co. GB-1353119, U.S. 3,780,124, DE-2213055, U.S. 3,696,164. (b) To American Cyanamid Co. U.S. 3,700,746. (c) S. Wang, X. An, Z. Cheng and H. Zhong, Linchan Huaxue Yu Gongye 16 (1996) 32.
D. Yin, Q. Li and D. Yin, Hunan Shifan Daxue Ziran Kexue Yuebao 18 (1985) 26.
Y. Fujihara, C. Hata and Y. Matubara, Yuki Gosei Kagaku Kyokaishi 32 (1974) 933.
Z.A. Flippenko, O.M. Baranov, G.N. Roganov and G.Y. Kabo, Chem. Nat. Compd. 21 (1985) 47.
Rudakow, Chem. Zentralbl 115(1) (1944) 16.
Treibs and Schmidt, Chem. Ber. 60 (1927) 2340.
To Hercules Powder Co. U.S. 2,402,898. (b) To Am. Cyanamid Co. U.S. 2,272,711.
To Am. Cyanamid Co. U.S. 2,399,739, U.S. 2,387,794, U.S. 2,388,359, U.S. 2,376,252, U.S. 2,376,308.
To Hercules Powder Co. U.S. 17,465,328.
Palmer, Ind. Eng. Chem. 34 (1942) 1028.
H. Pines, R.C. Olberg and V.N. Ipatieff, J. Am. Chem. Soc. 74 (1952) 4872.
R. Neumann and M. Lissel, J. Org. Chem. 54 (1989) 4607.
J. Ipaktschi and M. Brueck, Chem. Ber. 123 (1990) 1591.
D. Liu, Z. Sun and Q. Guo, Jingxi Huagong 15 (1998) 42. (b) Q. Guo, D. Liu and Z. Sun, Yantai Daxue Xuebag Ziran Kexue Yu Gongchenghan 12 (1999) 50.
P.A. Weyrich and W.F. Hoelderich, Appl. Catal. A: Gen. 158 (1997) 145.
D. Buhl, D.M. Roberge and W.F. Hoelderich, Appl. Catal. A: Gen. 188 (1999) 287.
S. Sivasanker and L.M. Yeddanapalli, Chem. Age of India 22 (1971) 622.
V. Krishnasamy and V. Mohan, J. Indian Chem. Soc. 60 (1983) 359. (b) V. Krishnasamy, Aust. J. Chem. 33 (1980) 1313.
E.N. Manukov, V.A. Chuiko and O.G. Vyglazov, Chem. Nat. Compd. 18 (1982) 242. (b) E.N. Manukov, V.A. Chuiko and O.G. Vyglazov, J. Org. Chem. USSR 20 (1984) 257.
G.A. Rudakov and G.A. Artamonov, J. Gen. Chem. 15 (1945) 75.
P. Ratnasamy, V. Krishnasamy and L.M. Yeddanapalli, Chem. Age India 22 (1971) 16.
G.A. Rudakov and A.T. Marchevskii, Sb. Statei Obschch. Khim 2 (1953) 1432.
L.M. Yeddanapalli and P. Desikan, J. Sci. Ind. Res. 18B (1959) 392.
P. Lesage, J.-P. Candy, C. Hirigoyen, F. Humblot, M. Leconte and J.-M. Basset, J. Mol. Catal. A: Chem. 112(2) 303.
P.W.N.M. van Leeuwen, C.F. Roobeek, J. Organomet. Chem. 258(3) (1983) 343–350. (b) L. Kollar, J. Bakos, B. Heil, P. Sandor and G. Szalontai, J. Organomet. Chem. 385 (1990) 147. (c) U. Azzena, G. Chelucci, G. Delogu, S. Gladiali and M. Marchetti, Gazz. Chim. Ital. 116 (1986) 307. (d) C. Abu-Gnim and I. Amer, J. Organomet. Chem. 516 (1996) 235. (e) F. Azzaroni, P. Biscarini, S. Bordoni and G. Longoni, J. Organomet. Chem. 508 (1996) 59. (f ) E.P. Romanenko, V.M. Tormyshev and V.D. Shteingarts, Russ. J. Org. Chem. 34(11) (1998) 1549.
J.-O. Zhou and H. Alper, J. Chem. Soc., Chem. Commun. 4 (1991) 233.
C.L. Kranemann and P. Eilbracht, Synthesis 1 (1998) 71.
A. de-O. Dias, R. Augusti, E.N.D. Santos and E.V. Gusevskaya, Tetrahedron Lett. 38 (1997) 41.
T. Chenal, R. Naigre, I. Cipres, P. Kalck, J.-C. Daran and J. Vaissermann, J. Chem. Soc., Chem. Commun. 9 (1993) 747. (b) R. Naigre, T. Chenal, I. Cipres, P. Kalck, J.-C. Daran and J. Vaissermann, J. Organomet. Chem. 480 (1994) 91.
J. Prandi, H.B. Kagan and H. Mimoun, Tetrahedron Lett. 27 (1986) 2617.
de P.A.L. Villa, B.F. Sels, D.E. de Vos and P.A. Jacobs, J. Org. Chem. 64 (1999) 7267.
J.M. Fraile, J.I. Garcia, J.A. Mayoral, L.C. de Menorval, F. Rachdi, J. Chem. Soc., Chem. Commun. (1995) 539.
R. Hutter, D.C.M. Dutoit, T. Mallat, M. Schneider and A. Baiker, J. Chem. Soc., Chem. Commun. 2 (1995) 163.
P. Laszlo, M. Levart and G.P. Singh, Tetrahedron Lett. 32 (1991) 3167.
E. Bouhtel, P. Laszlo, M. Levart, M.-T. Montaufier and G.P. Singh, Tetrahedron Lett. 34 (1993) 1123. (b) B.B. Wentzel, P.A. Gosling, M.C. Feiters and R.J.M. Notte, J. Chem. Soc., Dalton Trans. 13 (1998) 2241.
M.M. Reddy, T. Punniyamurthy and J. Iqbal, Tetrahedron Lett. 36 (1995) 159. (b) A.-J. Mandal, V. Khama and J. Iqbal, Tetrahedron Lett. 36 (1996) 3769. (c) A.K. Mandal and J. Iqbal, Tetrahedron 53 (1997) 7641. (d) T. Punniyamurthy, B. Bhatia, M.M. Reddy, G.C. Maikap and J. Iqbal, Tetrahedron 53 (1997) 7649.
N.Q. Prada, E.E. Stashenko, E.A. Paez and J.R. Martinez, Rev. Colomb. de Quim. 28 (1999) 45.
R. Baker, M. Borges, N.G. Cooke and R.H. Herbert, J. Chem. Soc., Chem. Commun. 6 (1987) 414. (b) R. Clarke, M. Gahagan, R.K. Mackie, D.F. Foster and D.J. Cole-Hamiliton, J. Chem. Soc., Dalton Trans. 7 (1995) 1221. (c) D. Juwiler, J. Blum and R. Neumann, J. Chem. Soc., Chem. Commun. 10 (1998) 1123. (d) H.E.B. Lempers, G.A. Ripolles and R.A. Sheldon, J. Org. Chem. 63 (1998) 1408.
P. Battioni, J.P. Renaud, J.F. Bartoli, M. Reina-Artiles, M. Fort and D. Mansuy, J. Am. Chem. Soc. 110 (1988) 8462. (b) A.M. Gonsalves, R.A.W. Johnstone, M.M. Pereira and J. Shaw, J. Chem. Soc., Perkin Trans. 1 (1991) 645. (c) S. Tangestaninejad and M. Moghadam, Synth. Commun. 28 (1998) 427. (d) S. Tangestaninejad and V. Mirkhani, J. Chem. Res. Synop. 12 (1998) 788. (e) S. Tangestaninejad and V. Mirkhani, Chem. Lett. 12 (1998) 1265. (f ) V. Mirkhani, S. Tangestaninejad and M. Moghadam, J. Chem. Res. Synop. 12 (1999) 722.
M. Bösing, A. Nöh, I. Loose and B. Krebs, J. Am. Chem. Soc. 120 (1998) 7252.
K.S. Ravikumar, F. Barbier, J.-P. Begue and D. Bonnet-Delpon, Tetrahedron 54 (1998) 7457.
R. Raja, G. Sankar and J.M. Thomas, Chem. Commun. 9 (1999) 829.
T.R. Boehlow and C.D. Spilling, Tetrahedron Lett. 37 (1996) 2717. (b) A.M. Al-Ajlauni and J.H. Espenson, J. Org. Chem. 61 (1996) 3969. (c) de P.A.L. Villa, D.E. de Vos, de C.C. Montes and P.A. Jacobs, Tetrahedron Lett. 39 (1998) 8521.
A. Deloffre, S. Halut, L. Salles, J.-M. Bregeault, J.R. Gregorio, B. Denise and H. Rudler, J. Chem. Soc., Dalton Trans. 17 (1999) 2897. See also; H. Rudler, J.R. Gregorio, B. Denise, J.-M. Bregeault and A. Deloffre, J. Mol. Catal. A: Chem. 133 (1998) 255.
V. Kesavan and S. Chandrasekaran, J. Chem. Soc. Perkin Trans. 1 21 (1997) 3115. (b) T.-S. Lai, H.-L. Kwong, R. Zhang and C.-M. Che, J. Chem. Soc., Dalton Trans. 21 (1998) 3559. (c) C.-J. Liu, W.-Y. Yu, S.-G. Li and C.-M. Che, J. Org. Chem. 63 (1998) 7364. (d) C.-J. Liu, W.-Y. Yu, C.-M. Che and C.-H. Y, J. Org. Chem. 64 (1999) 7365.
M.A. Aramerdia, V. Borav, C. Jirvenez, J.M. Luque, J.M. Marinas, F.J. Romero, J.R. Ruiz and F.J. Urbano, Stud. Surf. Sci. Catal. 130B (2000) 1667.
E. Herrero, S. Casuscelli, J. Fernandez, C. Poncio, M. Rueda and O. Oyola, Molecules 5 (2000) 336.
D.T. On, M.P. Kapoor, P.N. Joshi, L. Bonneviot and S. Kaliaguine, Catal. Lett. 44 (1997) 171.
J.-F. Zhang, Y.-H. Hu, Y.-ru. Li and D.-L. Yin, Zhongnan Gongye Daxue Yuebao, Z. Kekueban 32 (2001) 50.
T. Kamiyama, M. Inoue and S. Enomoto, Chem. Lett. (1989) 1129.
M.M. Reddy, T. Punniyamurthy and J. Iqbal, Tetrahedron Lett. 36 (1995) 159. (b) T. Takai, E. Hata, K. Yarozu and T. Mukiyama, Chem. Lett. 10 (1992) 2077. (c) B.C. Das and J. Iqbal, Tetrahedron Lett. 38 (1997) 1235. (d) G. Rothenberg, Y. Yatziv and Y. Sasson, Tetrahedron 54 (1998) 593.
H. Henning and D. Luppa, J. Prakt. Chem. 341 (1999) 757.
M.E. de Carvalho, B. Meunier, Tetrahedron Lett. 24 (1983) 3621. (b) P.L. Anelli, S. Banfi, F. Legramandi, F. Montanan, G. Pozzi and S. Quici, J. Chem. Soc., Perkin. Trans. 1 (1993) 1345. (c) A.P.H.J. Schenning, D.H.W. Hubert, J.H. van Esch, M.C. Feiters and R.J.M. Nolte, Angew. Chem. 106 (1994) 2587. (d) H. Henning, J. Behling, R. Meusinger and L. Weber, Chem. Ber. 128 (1995) 229. (e) L. Weber, I. Imiolczyk, G. Haufe, D. Rehorek and H. Henning, J. Chem. Soc., Chem. Commun. 4 (1992) 301.
A.M. Al-Ajlouni and J.H. Espenson, J. Org. Chem. 61 (1996) 3969.
W. Adam, C.R. Saha-Moeller and O. Weichold, J. Org. Chem. 65 (2000) 2897. (b) V.P. Rajan, S.N. Bannore, H.N. Subbarao and S. Dev, Tetrahedron 40 (1984) 983. (c) R.W. Saalfrank, S. Reihs and M. Hug, Tetrahedron Lett. 34 (1993) 6033. (d) S. Tangestaninejad and V. Mirkhani, J. Chem. Res. Synop. 12 (1998) 788. (e) S. Tangestaninejad and V. Mirkhani, Chem. Lett. 12 (1998) 1265. (f ) R. Clarke, M. Gahagan, R.K. Mackie, D.F. Foster and D.J. Cole-Hamiliton, J. Chem. Soc., Dalton Trans. 7 (1995) 1221. (g) S. Tangestaninejad and V. Mirkhani, J. Chem. Res. Synop. 12 (1998) 788. (h) P. Battioni, J.P. Renaud, J.F. Bartoli, M. Reina-Artiles, M. Fort and D. Mansuy, J. Am. Chem. Soc. 110 (1988) 8462. (i) T. Takai, E. Hata, K. Yarozu and T. Mukiyama, Chem. Lett. 10 (1992) 2077. ( j) V. Mirkhani, S. Tangestaninejad and M. Moghadam, J. Chem. Res. Synop. 12 (1999) 722.
M.M. Reddy, T. Punniyamurthy and J. Iqbal, Tetrahedron Lett. 36 (1995) 159. (b) B. Meunier, E. Guilmet, M-E de Canalho and R. Poilblanc, J. Am. Chem. Soc. 106 (1984) 6668. (c) P. Battioni, J.P. Renaud, J.F. Bartoli, M. Reina-Artiles, M. Fort and D. Mansuy, J. Am. Chem. Soc. 110 (1988) 8462.
O. Bortolini, S. Campestrini, F.Di. Furia, G. Modena and G. Valle, J. Org. Chem. 52 (1987) 5467.
M.F. Semmelhack, C.R. Schmid, D.A. Cortes and C.S. Chou, J. Am. Chem. Soc. 106 (1984) 3374. (b) I.E. Marko, A. Gautier, I. Chelle-Regnaut, P.R. Giles and M. Tsukazaki, J. Org. Chem. 63 (1998) 7576. (c) I.E. Marko, P.R. Giles, M. Tsukazaki, I. Chelle-Regnaut and A. Gautier, J. Org. Chem. 64 (1999) 2433.
T. Ounniyamurthy and J. Iqbal, Tetrahedron Lett. 35 (1994) 4007. (b) T. Punniyamurthy, B. Bhatia, M.M. Reddy, G.C. Maikop and J. Iqbal, Tetrahedron 53 (1997) 7649.
T. Nakano, Y. Ishii and M. Ogawa, J. Org. Chem. 52 (1987) 4855.
R. Kumar, G.C.G. Pais, B. Pandey and P. Kumar, J. Chem. Soc., Chem. Commun. 13 (1995) 1315.
T. Nishimura, N. Kakiuchi, M. Inoue and S. Uemura, Chem. Commun. 14 (2000) 1245.
E. Gomez-Bengoa, P. Noheda and A.M. Echavarren, Tetrahedron Lett. 35 (1994) 7097. (b) K. Kaneda, M. Fujii and K. Morioka, J. Org. Chem. 61 (1996) 4502. (c) K. Kaneda, Y. Fujii and K. Ebitani, Tetrahedron Lett. 38 (1997) 9023.
T. Matsushita, K. Ebitani and K. Kaneda, Chem. Commun. 3 (1999) 265.
A. Bleloch, B.F.G. Johnson, S.V. Ley, A.J. Price, D.S. Shephard and A.W. Thomas, Chem. Commun. 18 (1999) 1907.
M. Matsumoto and S. Ito, J. Chem. Soc., Chem. Commun. 17 (1981) 907. (b) M. Matsumoto and N. Watanabe, J. Org. Chem. 49 (1984) 3435. (c) G. Green, W.P. Griffith, D.M. Hollinshead, S.V. Ley and M. Schroeder, J. Chem. Soc., Perkin Trans. 1 4 (1984) 681. (d) T. Higuchi, H. Ohtake and M. Hirobe, Tetrahedron Lett. 32 (1991) 7435. (e) W.P. Griffith and J.M. Jolliffe, J. Chem. Soc., Dalton Trans. 24 (1992) 3483. (f ) A.J. Bailey, W.P. Griffith, A.J.P. White and D.J. Williams, J. Chem. Soc., Chem. Commun. 16 (1994) 1833. (g) A.J. Bailey, W.P. Griffith and P.D. Savage, J. Chem. Soc., Dalton Trans. 21 (1995) 3537. (h) D.D. Agarwal and R. Rastogi, Indian J. Chem., Sect. A 36 (1997) 164. (i) A. Dijksman, A. Arne, W.C.E. Isabel and R.A. Sheldon, Chem. Commun. 16 (1999) 1591.
K. Krohn, I. Vinke and H. Adam, J. Org. Chem. 61 (1996) 1467.
K. Kaneda, Y. Kawanishi and S. Teranishi, Chem. Lett. (1984) 1481.
N.P. Griffith and J.M. Jollifte, J. Chem. Soc., Dalton Trans. 24 (1992) 3483.
T. Punniyamurthy and J. Iqbal, Tetrahedron Lett. 35 (1994) 4007.
T. Nishimura, T. Onoue, K. Ohe and S. Uemura, J. Org. Chem. 64 (1999) 6750.
K.P. Volcho, N.F. Salakhutdinov and V.A. Barkhash, Russ. J. Org. Chem. 35 (1999) 1554. (b) N.F. Salakhutdinov, K.P. Volcho, P. Konstantin, I.V. Il'ina, D.V. Korchagina, L.E. Tatarova and V.A. Barkhash, Tetrahedron 54 (1998) 15619. (c) K.P. Volcho, D.V. Korchagina, L.E. Tatarova, N.F. Salakhutdinov and V.A. Barkhash, Russ. J. Org. Chem. 29 (1993) 541.
M.P. Doyle, L.C. Wang and K.-L. Loh, Tetrahedron Lett. 25 (1984) 4087.
M. Suda, Synthesis 9 (1981) 714.
T. Kuwata, J. Soc. Chem. Ind. Jpn. 39 (1936) 392–394. (b) T. Kuwata, J. Soc. Chem. Ind., Jpn. 42 (1939) 247.
T. Yamanaka, Bull. Chem. Soc. Jpn. 48 (1995) 3471.
Liu, Yaoquan, Chen, Qingzhi, Li, Yunlong, Linchan Huaxue Yu Gongye 9 (1989) 35.
P. Xiao, H. Wei and P. Xin, Xiangtan Daxue Ziran Kexue Xuebao 18(4) (1996) 56.
M. Nomura, S. Hisatomi, T. Hamada and Y. Fujihara, Nihon Yukagakkaishi 46 (1997) 583.
Q. Yang, J. Qi, J. Lin and X. Du, Linchan Huaxue Yu Gongye 17 (1997) 33.
D. Yin, W. Deng, Weiguo Hunan Shifan Daxue Ziran Kexue Xuebao 20 (1997) 52.
K. Hensen, C. Mahaim and W.F. Hoelderich, Appl. Catal. A: Gen. 149 (1997) 311.
H.-T. Li and D.-L. Yin, Fenzi Cuihua 13 (1999) 362.
J.C. Schmidhauser, G.L. Bryant, P.E. Donahue, M.F. Garbauskas and E.A. Williams, J. Org. Chem. 60 (1995) 3612. (b) E. Pottier, Bull. Soc. Chim. Fr. 9–10 (1981) 335.
T.F. Titova, V.V. Fomenko, D.V. Korchagina, N.F. Salakhutdinov, K.G. Ione and V.A. Barkhash, Russ. J. Org. Chem. 33 (1997) 671. (b) V.V. Fomenko, D.V. Korchagina, O.I. Yarovaya, Yu.V. Gatilov, N.F. Salakhutdinov, K.G. Ione and V.A. Barkhash, Russ. J. Org. Chem. 35 (1999) 1006.
K.P. Volcho, D.V. Korchagina, N.F. Salakhutdinov and V.A. Barkhash, Tetrahedron Lett. 37 (1996) 6181.
E.V. Kuzakov and E.N. Shmidt, Chem. Nat. Compd. 36 (2000) 245.
Clark, Hawkins, Ind. Eng. Chem. 33 (1941) 1174.
N. Ferret, L. Mussate-Mathieu, J.-P. Zahra and B. Waegell, J. Chem. Soc., Chem. Commun. (1994) 2589.
M.A. Schwegler and H. van Bekkum, Bull. Soc. Chim. Belg. 99 (1990) 113.
A.B. Radbil', M.V. Kulikov, T.N. Sokolova, V.R. Kartashov and B.A. Zolin, Chem. Nat. Compd. 35 (1999) 524.
K.P. Volcho, L.E. Tatarova, E.V. Suslov, D.V. Korchagina, N.F. Salakhutdinov and V.A. Barkhash, Russ. J. Org. Chem. 37 (2001) 1418.
J.C. van der Waal, M.S. Rigutto and H. van Bekkum, Appl. Catal. A: Gen. 167 (1998) 331.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Swift, K.A. Catalytic Transformations of the Major Terpene Feedstocks. Topics in Catalysis 27, 143–155 (2004). https://doi.org/10.1023/B:TOCA.0000013549.60930.da
Issue Date:
DOI: https://doi.org/10.1023/B:TOCA.0000013549.60930.da