Carbenoid reaction: The reaction of dibromodiphenylmethane 9,9-dibromofluorene and 9,9-dichloro-9H-tribenzo[a.c.e] cycloheptene with alkyllithium in the presence of olefins | Health & Environmental Research Online (HERO)

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HERO ID

6169553

Reference Type

Journal Article

Title

Carbenoid reaction: The reaction of dibromodiphenylmethane 9,9-dibromofluorene and 9,9-dichloro-9H-tribenzo[a.c.e] cycloheptene with alkyllithium in the presence of olefins

Author(s)

Moritani, I; Murahashi, S

Year

1967

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Journal

Tetrahedron
ISSN: 0040-4020

Volume

Issue

Page Numbers

3631-3643

DOI

10.1016/0040-4020(67)80009-7

URL

http://www.sciencedirect.com/science/article/pii/0040402067800097
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Abstract

1,1-Diphenyl-2-ethoxycyclopropane was obtained from the reaction of dibromodiphenyl-methane (II) with methyllithium in the presence of ethyl vinyl ether. A cyclopropane derivative was not obtained from the reaction of 9,9-dibromofluorene (III) or 9,9-dichloro-9H-tribenzo[a.c.e]cycloheptene (IV) with alkyllithium in olefin but 9,9′-bifluorenylidene (IX) and 9,9′-dibromo-9,9′-bifluorenyl (XI) were produced from III and 9-methylene-9H-tribenzo[a.c.e]cycloheptene (XXIII) and 9H-tribenzo-[a.c.e]-cyclohepten-9-ol (XXIV) from IV. The mechanism of the reaction is discussed.