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Photochemische Reaktionen. 50. Mitteilung [1]. Zur Photochemie von gesättigten β‐Ketosulfiden II . Synthese von 6‐Hydroxy‐2‐thia‐7‐oxa‐isotwistan
Author(s) -
Ganter C.,
Moser J.F.
Publication year - 1969
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.19690520322
Subject(s) - chemistry , excited state , methanol , solvent , benzene , photochemistry , stereochemistry , ultraviolet , medicinal chemistry , crystallography , organic chemistry , physics , quantum mechanics , nuclear physics
The results of the ultraviolet irradiation of the saturated β‐ketosulfide 2 are discussed. The photochemistry of 2 is characterized by the occurrence of two primary photoprocesses. Their efficiences depend markedly on the excited transition, (charge‐transfer)‐ or ( n → π*)‐excitation, respectively. In methanol solution (charge‐transfer)‐excitation leads almost exclusively to product 7 , due to (C α – S)‐fission, and ( n → π*)‐excitation to nearly equal amounts of 7 and of products 4 and 6 which result from α‐cleavage. On solvent sensibilization in benzene products 4, 6, 7 and the still unidentified product 5 2 are formed. Compounds 4 and 6 have been described earlier [2]. The structure elucidation of 7 is reported in this paper. Acid‐induced transformation of 7 yields the dihetero‐isotwistane 15 .