Abstract
The title compounds are difunctionalized acetylenic building blocks, which can serve as electrophilic dienophiles and dipolarophiles in [4+2] and azide-iodoalkyne [3+2] cycloaddition reactions, which, however, require strong thermal activation. In their crystal structures, they are self-complementary tectons, which are arranged in polymeric chains maintained by very short intermolecular Csp–I···O=P halogen bonds.
Acknowledgements
We thank B. Müller (Institute of Inorganic Chemistry II) for the X-ray diffraction data collection and Dr. M. Wunderlin for the mass spectra.
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: Ulm University.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Desiraju, G. R., Ho, P. S., Kloo, L., Legon, A. C., Marquardt, R., Metrangolo, P., Politzer, P., Resnati, G., Rissanen, K. Pure Appl. Chem. 2013, 85, 1711–1713.10.1351/PAC-REC-12-05-10Search in Google Scholar
2. Cavallo, G., Metrangolo, P., Milani, R., Pilati, T., Priimagi, A., Resnati, G., Terraneo, G. Chem. Rev. 2016, 116, 2478–2601.10.1021/acs.chemrev.5b00484Search in Google Scholar PubMed PubMed Central
3. Metrangolo, P., Resnati, G., Eds. Halogen Bonding: Fundamentals and Applications, Struct. Bond., Vol. 126; Springer: Berlin, Heidelberg, 2008.10.1007/978-3-540-74330-9Search in Google Scholar
4. MetrangoloP., ResnatiG., Eds. Halogen Bonding I: Impact on Materials Chemistry and Life Sciences, Top. Curr. Chem., Vol. 358; Springer International Publishing: Cham, Switzerland, 2015.10.1007/978-3-319-14057-5Search in Google Scholar
5. Clark, T., Hennemann, M., Murray, J. S., Politzer, P. J. Mol. Model. 2007, 13, 291‒296.10.1007/s00894-006-0130-2Search in Google Scholar PubMed
6. Politzer, P., Lane, P., Concha, M. C., Yuguang, M., Murray, J. S. J. Mol. Model. 2007, 13, 305–311.10.1007/s00894-006-0154-7Search in Google Scholar PubMed
7. Politzer, P., Murray, J. S., Clark, T. σ-Hole Bonding: A Physical Interpretation. In Halogen Bonding I: Impact on Materials Chemistry and Life Sciences, Top. Curr. Chem., Vol. 358, MetrangoloP., ResnatiG., Eds. Springer International Publishing: Cham, Switzerland, 2015; pp. 19–42.10.1007/128_2014_568Search in Google Scholar PubMed
8. Lommerse, J. P. M., Stone, A. J., Taylor, R., Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108–3116.10.1021/ja953281xSearch in Google Scholar
9. Chesnut, D. B., Savin, A. J. Am. Chem. Soc. 1999, 121, 2335–2336.10.1021/ja984314mSearch in Google Scholar
10. Stefan, T., Janoschek, R. J. Mol. Model. 2000, 6, 282–288.10.1007/PL00010730Search in Google Scholar
11. Le Questel, J.-Y., Laurence, C., Graton, J. CrystEngComm 2013, 15, 3212–3221.10.1039/c2ce26749gSearch in Google Scholar
12. Dumele, O., Wu, D., Trapp, N., Goroff, N., Diederich, F. Org. Lett. 2014, 16, 4722‒4725.10.1021/ol502099jSearch in Google Scholar PubMed
13. Oakdale, J. S., Sit, R. K., Fokin, V. V. Chem. Eur. J. 2014, 20, 11101–11110.10.1002/chem.201402559Search in Google Scholar PubMed PubMed Central
14. Padovan, P., Tartaggia, S., Lorenzon, S., Rosso, E., Zonta, C., De Lucchi, O., Fabris, F. Tetrahedron Lett. 2009, 50, 1973–1976.10.1016/j.tetlet.2009.02.064Search in Google Scholar
15. Vuilhorgne, M., Malpart, J., Mutti, S., Mignani, S. J. Heterocycl. Chem. 2003, 40, 159–160.10.1002/jhet.5570400122Search in Google Scholar
16. Charrier, C., Simonnin, M. P., Chodkiewicz, W., Cadiot, P. Comp. Rend. 1964, 258, 1537‒1540.Search in Google Scholar
17. Charrier, C., Chodkiewicz, W., Cadiot, P. Bull. Soc. Chim. Fr. 1966, 1002‒1011.Search in Google Scholar
18. For a modified preparation of 4, see: Peng, L., Xu, F., Shinohara, K., Nishida, T., Wakamatsu, K., Orita, A., Otera, J. Org. Chem. Front. 2015, 2, 248–252.10.1039/C4QO00325JSearch in Google Scholar
19. Huc, V., Balueva, A., Sebastian, R., Caminade, A., Majoral, J. Synthesis 2000, 726‒730.10.1055/s-2000-6402Search in Google Scholar
20. Hofmeister, H., Annen, K., Laurent, H., Wiechert, R., Chem, A. Int. Ed. Engl. 1984, 23, 727‒729.10.1002/anie.198407271Search in Google Scholar
21. Lommerse, J. P. M., Stone, A. J., Taylor, R., Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108–3116.10.1021/ja953281xSearch in Google Scholar
22. Bondi, A. J. Phys. Chem. 1964, 68, 441‒451.10.1021/j100785a001Search in Google Scholar
23. Aakeröy, C. B., Wijethunga, T. K., Desper, J., Đaković, M. Crystal Growth Des. 2015, 15, 3853–3861.10.1021/acs.cgd.5b00478Search in Google Scholar
24. Senderikhin, A. I., Dogadina, A. V., Ionin, B. I., Petrov, A. A. Zh. Obshch. Khim. 1988, 58, 1662‒1663.Search in Google Scholar
25. Acheson, R. M., Ansell, P. J. J. Chem. Soc., Perkin Trans. 1987, 1, 1275–1281.10.1039/p19870001275Search in Google Scholar
26. Tverdomed, S. N., Kolanowski, J., Lork, E., Röschenthaler, G. V. Tetrahedron 2011, 67, 3887‒3903.10.1016/j.tet.2011.03.076Search in Google Scholar
27. Review: Duda, B., Tverdomed, S., Röschenthaler, G.-V. J. Fluor. Chem. 2013, 152, 29‒37.10.1016/j.jfluchem.2013.02.006Search in Google Scholar
28. Hein, J. E., Tripp, J. C., Krasnova, L. B., Sharpless, K. B., Fokin, V. V. Angew. Chem. Int. Ed. 2009, 48, 8018‒8021.10.1002/anie.200903558Search in Google Scholar
29. Lequan, R.-M., Pouet, M.-J., Simonnin, M.-P. Org. Magn. Reson. 1975, 7, 392‒400.10.1002/mrc.1270070808Search in Google Scholar
30. Corriu, R. J. P., Guérin, C., Henner, B. J. L., Jolivet, A. J. Organomet. Chem. 1997, 530, 39–48.10.1016/S0022-328X(96)06655-7Search in Google Scholar
31. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed
32. Sheldrick, G. M. Acta Crystallogr. 2015, C71, 3–8.Search in Google Scholar
33. Farrugia, L. J. J. Appl. Cryst. 2012, 45, 849–854.10.1107/S0021889812029111Search in Google Scholar
34. Mercury (version 3.6). Cambridge Crystallographic Data Centre: Cambridge (U. K.), 2001‒2015.Search in Google Scholar
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