
TY  - JOUR
A1  - Baxter, GJ 
A1  - Brown, RFC 
T1  - Methyleneketenes and methylenecarbenes. XI. Rearrangements of cycloalkylidenecarbenes
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1978
VL  - 31
IS  - 2
SP  - 327
EP  - 339
KW  - 
UR  - https://doi.org/10.1071/CH9780327 
N2  - 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). 
ER  -

