Carbanionic rearrangements of halomethylenecycloalkanes

SP Samuel, TQ Niu, KL Erickson

Index: Samuel, Steve P.; Niu, Tian-qi; Erickson, Karen L. Journal of the American Chemical Society, 1989 , vol. 111, # 4 p. 1429 - 1436

Full Text: HTML

Citation Number: 26

Abstract

Abstract: The mechanism for the unusual base-induced ring-enlargement reaction of (halomethy1ene) cyclobutanes to 1-halocyclopentenes was examined by C-13 labeling studies with (bromomethy1ene) cyclobutane (l), cis-and trans-1-(bromo-methylene)-3-ethoxy- 2, 2-dimethylcyclobutane (15 and 16), and l-(bromomethylene)-2, 2, 4, 4- tetramethylcyclobutane (22). Two competing processes were found to lead from the vinyl ...