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Reactions of Substituted (1,3‐Butadiene‐1,4‐diyl)magnesium, 1,4‐Bis(bromomagnesio)butadienes and 1,4‐Dilithiobutadienes with Ketones, Aldehydes and PhNO To Yield Cyclopentadiene Derivatives and N‐Ph Pyrroles by Cyclodialkenylation
Author(s) -
Fang Hongyun,
Li Guotao,
Mao Guoliang,
Xi Zhenfeng
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400025
Subject(s) - chemistry , reagent , cyclopentadiene , moiety , magnesium , reactivity (psychology) , yield (engineering) , organic chemistry , aldehyde , medicinal chemistry , pyrrole , ketone , catalysis , medicine , materials science , alternative medicine , pathology , metallurgy
1,4‐Dilithiobutadiene derivatives 1 , 1,4‐bis(bromomagnesio)butadiene derivatives 2 and metallacyclic (1,3‐butadiene‐1,4‐diyl)magnesium reagents 3 were prepared and their reactions with ketones, aldehydes, and PhNO were investigated. Multiply substituted cyclopentadienes and N‐Ph pyrroles were formed by unprecedented reaction conditions. The carbonyl group of aldehydes and ketones was deoxygenated during the reaction and behaved formally as a one‐carbon unit; the NO moiety of PhNO was cleaved to afford N‐Ph pyrrole derivatives. Furthermore, different reactivities among these three types of reagents 1 , 2 and 3 were revealed. The 1,4‐dilithium reagents 1 readily reacted with both aldehydes and ketones; the 1,4‐dimagnesium reagents 2 reacted with aldehydes, but not ketones; the metallacyclopentadiene reagents of magnesium 3 showed higher reactivity and did react with ketones.