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Intramolecular photocyclization of cis, cis- and trans, trans-cyclodeca-1,6-diene to anti tricyclo[5.3.0.02,6]decane.

✍ Scribed by Arnon Shani

Publisher: Elsevier Science
Year: 1972
Tongue: French
Weight: 131 KB
Volume: 13
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)84380-x

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✦ Synopsis

The transannular photocyclization of the cis,cis-cyclodecs-1,6+lienes to the tricyolo 5.3.0.02p6 --C 3 decane (1) may be explained due to the proximity in space of the two double bonds in the ~~hamnocks conformation I (2). Hence, in an intramolecular photocyclization of the isomeric trans,trans,cyclodeca-1,6-diene, both chair conformation IIa aad the twisted conformation IIb must be considered. An inspection of Dreiding models indicated that the distances between Cl-C7 and C2-C6 in I are 1.8 1, while in IIa these distances are 2.8 1 and in IIb the distances between C,-C6 and C2-C7 are 1.0 X.

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