
%0 Journal Article
%A Baxter, GJ 
%A Brown, RFC 
%T Methyleneketenes and methylenecarbenes. XI. Rearrangements of cycloalkylidenecarbenes
%J Australian Journal of Chemistry
%D 1978/02/01
%V 31
%N 2
%P 327-339
%K 
%R https://doi.org/10.1071/CH9780327
%U https://www.publish.csiro.au/paper/CH9780327 
%X The products of flash vacuum pyrolysis of the cycloalkylidene derivatives (3) of Meldrum's acid at 480-640&#176; 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). 
