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Photochemistry of Spiro[6H-[1,3]Oxathiin-2,2′-tricyclo[3.3.1.13,7]decan]- 6-one

✍ Scribed by Kerstin Schmidt; Paul Margaretha

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
137 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

On irradiation (300 nm) in the solid state, the title compound 8 affords tricyclo[3.3.1.1^3,7^]decan‐2‐one (=adamantan‐2‐one; 9) selectively via [4+2] cycloreversion. A similar result is obtained on photolysis in solution (MeCN or acetone), also in the presence of added alkenes. On irradiation in MeOH, a solvent adduct 11 is isolated in addition to 9. From experiments in CD~3~OD, it can be inferred that 11 is formed via syn‐addition of MeOH to the ground‐state (E)‐heterocycle 16.

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