Summary
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1.
An investigation has been made of the ability of 2,6-dimethoxy-α-methylstyrene and of 4-tert-butyl-α,2,6-trimethylstyrene to undergo polymerization and it has been found that neither of these compounds is able to polymerize.
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2.
It has been suggested that the inability of 2,6-dimethoxy-α-methylstyrene and 4-tert-butyl-α,2,6-trimethylstyrene to undergo polymerization is to be explained by stereochemical considerations, namely by the steric obstacles created by the α-methyl group and the two ortho-substituents.
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3.
It has been found that 4′-tert-butyl-2′,6′-dimethylacetophenone does not react with organomagnesium compounds, but readily undergoes Shorygin's reaction with organosodium compounds.
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4.
2,6-Dimethoxy-α-methylstyrene and 4-tert-butyl-α,2,6-trimethylstyrene have been synthesised.
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Literature Cited
V. V. Korshak and N. G. Matveeva, Bull. Acad. Sci., USSR, Div. Chem. Sci., No. 3, 542 (1953).
V. V. Korshak and N. G. Matveeva, Proc. Acad. Sci. USSR, 78, 1145 (1951).
V. V. Korshak and N. G. Matveeva, Bull. Acad. Sci. USSR, Div. Chem. Sci. No. 3, 547 (1953).
V. V. Korshak and N.G. Matveeva, Bull. Acad. Sci. USSR, Div. Chem. Sci. No. 2. 344 (1953).
P. P. Shorygin, Investigations on Organosodium Compounds, Moscow, 1910, p. 6.
V. V. Korshak, Bull. Acad Sci. USSR Div. Chem. Sci. No. 3. 269 (1949).
V. V. Korshak, Chemistry of Macromolecular Compounds, Acad. Sci USSR Press, Moscow and Leningrad, 1950, p. 180.
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Korshak, V.V., Matveeva, N.G. Macromolecular compounds Communication 59. Stereochemistry of α-methylstyrenes in its relation to their tendency to undergo polymerization. Russ Chem Bull 2, 675–678 (1953). https://doi.org/10.1007/BF01171792
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DOI: https://doi.org/10.1007/BF01171792