Summary
-
1.
It was shown that 2-methyl-2-phenylpropylmagnesium chloride does not react with isobutyl halides, but it condenses with allyl and 2-methylallyl chlorides with formation of the corresponding hydrocarbons in high yield (70% and 51%).
-
2.
The freezing points of the branched alkylbenzenes and alkylcyclohexanes synthesized range from −70° to −90° and are lower by 30–45° than the freezing points of the isomeric hydrocarbons having normal paraffin chains.
Literature cited
E. Schreiner, J. prakt. Chem. 82, 292 (1910); O. Halse, J. prakt. Chem. 89, 451 (1914); R. Huston et al,. J. Org. Chem. 3, 251, 351 (1938); 6, 252 (1941); 11, 657 (1946); 13, 63 (1948); 18, 620 (1953).
R. Huston, et al., J. Am. Chem. Soc. 70, 1090 (1948).
R. Paquette, E. Lingafelter, and H. Tartar, J. Am. Chem. Soc. 65, 686 (1943).
A. Schmidt, and A. Grosser, Ber. 73, 930 (1940).
V. Weinmayr, US Patent 2467170; C. A. 43, 6232 (1949).
W. Smith jun, and D. Sellas, Organic Syntheses, Collection 4 (Russian Translation), Moscow, Foreign Lit. Press. 1953, p. 526.
S. Birch, R. Dean, F. Fidler, and R. Lowry, J. Am. Chem. Soc. 71, 1361 (1949).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Petrov, A.D., Nefedov, O.M. & Ogibin, Y.N. Reaction of 2-methyl-2-phenylpropylmagnesium chloride with allyl and 2-methylallyl chlorides. Russ Chem Bull 6, 1035–1037 (1957). https://doi.org/10.1007/BF01173607
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01173607