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Remarkably fast [2+2]cycloreversion in methoxy substituted Cookson's cage ketones assisted by the capto-dative substituent effect and by the through-bond interaction

✍ Scribed by Yasushi Okamoto; Ken Kanematsu; Teruyo Fujiyoshi; Eiji Osawa

Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 242 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)94163-7

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✦ Synopsis

1,7-Dimethoxy groups in Cookson's pentacyclic cage ketone derivatives (2 and 2) accelerate the thermal [2+2]cycloreversion, possibly by means of the unusual lengthening of Cl-C7 bond and the synergetic capto-dative stabilization of 1,4_diradical (7, and 8).