Photochemistry of phthaloylcysteine, its methyl ester and C-unprotected S-alkyl derivatives

Autor:	Axel G. Griesbeck, Paul Dallakian, Wolfgang Kramer, Joachim Hirt
Rok vydání:	1998
Předmět:	chemistry.chemical_classification Decarboxylation Organic Chemistry Photochemistry Biochemistry Homolysis Electron transfer chemistry.chemical_compound chemistry Excited state Drug Discovery Acetone Singlet state Acetonitrile Alkyl
Zdroj:	Tetrahedron. 54:3169-3180
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(98)00063-5
Popis:	N-Phthaloyl cysteine derivatives 1a-d were photochemically transformed by elimination, decarboxylation, and via electron transfer cyclization to the products 2,3,4 and 6–8. The spin selectivities of singlet and triplet pathways were investigated in acetonitrile and acetone. The excited singlets were prone to elimination and γ-H abstractions (e.g. formation of 5) whereas the triplets cyclized to thiazinoisoindoles. This behaviour can be correlated with the efficiencies of forward and return electron transfer steps versus homolytic hydrogen abstractions as examplified for the cysteine substrate 9.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8e32a3d12f3d87fb505db33e0a54b4ff https://doi.org/10.1016/s0040-4020(98)00063-5 Zobrazit plný text záznamu Full Text from ScienceDirect