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The Photoisomerization of 1,2,3,4,5-Pentamethyl-5-vinyl-1,3-cyclopentadiene

✍ Scribed by Ulrich Burger; Robert Etienne

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
377 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The title compound 1 is shown to give, both upon direct irradiation at 254 nm and upon acetophenone‐sensitized photolysis at 300 nm, the syn‐vinyl‐pentamethylhousene 5, which spontaneously rearranges in a [3,3]0sigmatropic process to give the bicyclo[3.2.0]heptadiene skeleton 2. Based on the photochemical behaviour of selectively deuterated starting material, the suggestion is made that the direct photolysis produces the vinylhousene skeleton by a classic electrocyclization, whereas the sensitized reaction reaches the same target via a di‐π‐methane rearrangement. The bicyclo[3.2.0]heptadiene derivative 2 give pentamethylhomoprismane 3 upon prolonged irradiation at 254 nm.

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