The camphoketene dimers

✍ Scribed by Peter Yates; E.A. Chandross

• Book ID: 104249958
• Publisher: Elsevier Science
• Year: 1959
• Tongue: French
• Weight: 234 KB
• Volume: 1
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99476-6

✦ Synopsis

TREATMENT of an ethereal solution of d-camphor-3-carbonyl chloride (I) with quinoline or triethylamine yields two isomeric products, C&iS804, which . were considered by Staudlnger and SchotzL to be stereoisomers of the l,?Lcyclobutauedione derivative II, arising by dimerizatlon of "camphoketene" (III). Pyrolysis of these csmphoketene dimers or of I gives a third isomer which has been assigned structure IV.

1 We now propose that the camphoketene dimers be assigned structure IV and the pyrolysis product structure V. These proposals serve to rationalize all the previously reported data, Including results explicable only with difficulty on the basis of the earlier formulations, and are uniquely in accord with the new data now to be presented.

' Ii. Staudlnger and S. Schotz, Bz 22, 1105 (1920).