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- Title
Photochemische Reaktionen. 62. Mitteilung [1]. Die Photofragmentierung von O-acetyljervin.
- Authors
Baggiolini, E.; Berscheid, H. G.; Bozzato, G.; Cavalieri, E.; Schaffner, K.; Jeger, O.
- Abstract
On ultraviolet irradiation O-acetyljervine ( 1) is subjected to several parallel fragmentations. From the complex reaction mixtures obtained in a variety of solvents (dioxan, tetrahydrofuran, acetonitrile, iso-octane, benzene) the major alicyclic products 6- 8 and the heterocyclic compounds 12- 16 have been isolated. Products 6- 8 undergo further photochemical changes, e.g., decarbonylation of 7 to 9 and hydrolytic cleavage of 8 to 10. These photofragmentations are initiated almost specifically upon selective π → π* excitation at 2537 Å with a quantum yield of Φ2537 = 0.145 for conversion of starting material. Reaction upon irradiation in the long-wavelength n → π* absorption band is very much less efficient (Φ3660 = 0.611 · 10−3, both determinations for O-trimethylsilyl-jervine ( 2) in tetrahydrofuran). A high degree of photostability is observed also at 2537 Å on N-protonation of O-acetyljervine ( 1) in acetic acid. Furthermore, reactivity is greatly reduced for the N-methyl ( 3) and N-acetyl ( 4) derivatives in neutral solvents at 2537 Å. N-Chloro-O-acetyljervine ( 5) in dioxan at 2537 Å gave preferentially O-acetyljervine hydrochloride.
- Publication
Helvetica Chimica Acta, 1971, Vol 54, Issue 2, p429
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19710540202