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On the Stability of Disubstituted Cyclobutenes – A Computational Study
Author(s) -
Maryasin Boris,
Maulide Nuno
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801243
Subject(s) - chemistry , nucleophile , electrophile , bicyclic molecule , alkylation , ring (chemistry) , computational chemistry , lactone , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
A computational study of the electrocyclic ring‐opening of 2‐substituted cyclobutenecarboxylic acids is presented. Detailed calculations suggest a model to predict whether the product of nucleophilic alkylation of a bicyclic lactone electrophile will be a cyclobutenecarboxylic acid or its dienoic acid isomer, based on the used nucleophile.