✦ LIBER ✦

Photochemical reactions of mercapto/amino substituted alkyl phenylglyoxylates induced by intramolecular electron transfer

✍ Scribed by Shengkui Hu; Douglas C. Neckers

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 750 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00044-6

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✦ Synopsis

2'-Alkylthio ethyl phenylglyoxylates (1) and 2'-dimethylamino ethyl phenylglyoxylate (10) were synthesized and their photochemistry studied. In contrast to their oxygen analogs 3, which give normal Norrish type H cleavage products, the title compounds undergo intermolecular electron transfer from the heteroatom (sulfur/nitrogen) to the excited carbonyl group, followed by proton transfer and subsequent closing of the resulting biradicals to produce seven-membered (2 )/five-membered (11) lactones in high yield Thiadialkyl phenylglyoxylates (9) react inefficiently due to intramolecular self-quenching of phenylglyoxylate chromophores. The photoreactivity of a-oxothioester ( 14) was compared with that of its nitrogen (a-oxoamide) and oxygen (phenylglyoxylate) counterparts.

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