Effect of pressure on structural and steric orientation in diene synthesis. Communication 1. Condensation of 1-vinylcyclopentene with methyl acrylate

Effect of pressure on structural and steric orientation in diene synthesis. Communication 1. Condensation of 1-vinylcyclopentene with methyl acrylate Full article

Journal

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science
ISSN: 2376-8444 , E-ISSN: 0568-5230

Output data

Year: 1964, Volume: 13, Number: 6, Pages: 1003-1008 Pages count : 6 DOI: 10.1007/bf01141656

Authors

El'yanov B.S. ¹ , Rudenko B.A. ¹ , Gonikberg M.G. ¹ , Kucherov V.F. ¹

Affiliations

1	N. D Zelinskii Institute of Organic Chemistry, Academy of Sciences, USSR

1. Increase in pressure from atmospheric to 6000 Kg/cm2 leads to a change in structural and steric orientation in the diene condensation of 1-vinylcyclopentene with methyl acrylate which favors the formation of the ortho-cis isomer. The relative amounts of the other three isomers scarcely change when pressure is applied. 2. For the analysis of the volume effects of activation in the system studied a cyclic transition state was assumed with a structure intermediate between that of a model with a parallel arrangement of the planes of the diene and dienophile, on the one hand, and the structure of the adduct, on the other. Such a transition state is in full accord with the experimental data obtained. 3. In the reaction studied the relative amounts of the stereoisomeric ortho adducts are determined mainly by electronic, not steric, effects.

El'yanov B.S. , Rudenko B.A. , Gonikberg M.G. , Kucherov V.F.
Effect of pressure on structural and steric orientation in diene synthesis. Communication 1. Condensation of 1-vinylcyclopentene with methyl acrylate
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1964. V.13. N6. P.1003-1008. DOI: 10.1007/bf01141656 OpenAlex

OpenAlex:

W1993465322

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