Polar substituent effects in 1, 3-disubstituted bicyclo [1.1. 1] pentanes

DE Applequist, TL Renken…

文献索引：Applequist, Douglas E.; Renken, Terry L.; Wheeler, James W. Journal of Organic Chemistry, 1982 , vol. 47, # 25 p. 4985 - 4995

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被引用次数: 37

摘要

A different kind of instability of the bicyclopentane ring system was encountered in an attempt to prepare the 3-bromo carboxylic acid. Bromo ester 26 was prepared from 20 by the Cristol-Firth-Hunsdiecker reaction in 68% yield. Attempts to hydrolyze 26 with acid or base gave complex mixture8 of unidentified materials, Compound 26 also reacted immediately with silver nitrate in 95% ethanol or water. In water the major product was hydroxy ester 27 ...