Reaction of the tetrachlorocyclopropane (4, X = OH) with 3.2 molecular equivalents of methyllithium at 0-degrees-C leads to an ca. 6:5 mixture of diastereomeric allenes (5). Reaction of (13) with 2.5 mol. equiv. of methyllithium at -105 to -90-degrees-C leads to isomeric but-3-en-1-ols (14). The reactions may be explained in terms of an anion promoted hydrogen shift in an intermediate cyclopropane or vinylcarbene.
Dulayymi, Juma'a R. Al; Baird, Mark S.; Chakravarthy, Leela, Journal of Chemical Research, Miniprint, 1994, # 9, p. 1901 - 1916
作者:Dulayymi, Juma'a R. Al、Baird, Mark S.、Chakravarthy, Leela
DOI:——
日期:——
An unusual rearrangement of isoxazoles to 2-alkenoylpyrroles or 1-azafulvenes
作者:Ahmad R. Al Dulayymi、Mark S. Baird、William Clegg
DOI:10.1016/s0040-4039(97)10165-4
日期:1997.11
Intramolecular interaction of vinylcarbenes derived from 1,2-dichlorocyclopropenes with isoxazoles or bicyclic isoxazolines can lead to a rearrangement with the formation of 1-azafulvenes or derived 2-alkenoylpyrroles.