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Ring‐Opening Reaction of Methylenecyclopropanes Derived from Methylenecyclopropyl Aldehydes through Cope Rearrangement
Author(s) -
Tang XiangYing,
Wei Yin,
Shi Min
Publication year - 2010
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.201000880
Subject(s) - chemistry , cyclopentene , cope rearrangement , methylene , tandem , wittig reaction , bromide , rearrangement reaction , medicinal chemistry , ring (chemistry) , combinatorial chemistry , organic chemistry , catalysis , materials science , composite material
Tandem Wittig reaction/Cope rearrangement of methylenecyclopropyl aldehydes 1 with cinnamyltriphenylphosphonium bromide afforded a convenient method for the synthesis of cyclopentene derivatives 2 in moderate yields in a one‐pot manner. Dialkyl 2‐[(2‐methylenecyclopropyl)methylene]malonates 3 derived from methylenecyclopropyl aldehydes 1 could produce two kinds of cyclopentene derivatives, 4 and 5 , in good total yields through a thermally induced Cope rearrangement upon heating at 100 °C. Plausible reaction mechanisms are discussed on the basis of previous reports and on control experiments.