Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Methyleneketenes and methylenecarbenes. XI. Rearrangements of cycloalkylidenecarbenes

GJ Baxter and RFC Brown

Australian Journal of Chemistry 31(2) 327 - 339
Published: 1978

Abstract

The products of flash vacuum pyrolysis of the cycloalkylidene derivatives (3) of Meldrum's acid at 480-640° are rationalized in terms of formation of the cycloalkylidenecarbenes (1; ring size n = 4-8)and their rearrangement to cycloalkynes, to bicyclic cyclopropenes (e.g. (7)), or to further products derived from these. Pyrolysis of the 3,3-dimethylcyclobutylidene derivative (3h) gave 3,5-dimethylphenol, probably formed by cyclization of the (Z)-hexatrienone (22).    

The tetrahydrofuran-3-ylidene derivative (3i) gave butatriene and formaldehyde as major products of pyrolysis; these may be formed by retro-Diels-Alder fission of the heterocycloalkyne (27).

https://doi.org/10.1071/CH9780327

© CSIRO 1978

Committee on Publication Ethics


Export Citation Get Permission

View Dimensions