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Photochemistry of Spiro[6 H ‐[1,3]Oxathiin‐2,2′‐tricyclo[3.3.1.1 3,7 ]decan]‐ 6‐one
Author(s) -
Schmidt Kerstin,
Margaretha Paul
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490169
Subject(s) - chemistry , adduct , acetone , photodissociation , solvent , irradiation , photochemistry , solid state , medicinal chemistry , ground state , organic chemistry , physics , quantum mechanics , nuclear physics
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 .