Photochemical studies on the through-space S…S interaction of 2-phenylnaphtho[1,8-de][1,3]dithiin 1-oxide, 5-phenyl[1]benzothieno[4,3,2-def][1,3]benzodithiepin 4-oxide, and 2-phenyldibenzo[d,f][1,3]dithiepin 1-oxide

Autor:	Ohgi Takahashi, Ernst Horn, Hiroki Kusanagi, Takayoshi Fujii, Naomichi Furukawa
Rok vydání:	1999
Předmět:	Benzaldehyde chemistry.chemical_compound chemistry Ab initio quantum chemistry methods Organic Chemistry Drug Discovery Disulfide bond Oxide Photochemistry Biochemistry
Zdroj:	Tetrahedron. 55:5027-5046
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(99)00201-x
Popis:	2-Phenylnaphtho[1,8-de][1,3]dithiin 1-oxide (4a), 5-phenyl[1]benzothieno[4,3,2-def][1,3]benzodithiepin 4-oxide (4b), and 2-phenyldibenzo[d,f][1,3]dithiepin 1-oxide (4c) underwent facile consecutive photochemical reactions to give the corresponding disulfide, naphtho[1,8-cd][1,2]dithiole (1a), [1]benzothieno[4,3,2-cde][1,2]benzodithiin (1b), and dibenzo[c,e][1,2]dithiin (1c) and benzaldehyde (7), respectively, via the sulfur-sulfur (S…S) interaction. The proposed mechanism for these photochemical reactions is based on the quantum yields measurements, photo-intensity effects, and sensitizer effects. Ab initio calculations were also carried out for a model compound of the primary photoproduct, which showed that the S…S distance becomes shorter and the S-O distance becomes longer upon the excitation to the S1 state.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9cfa76b4a44b41cc43097e5fca7fc1e0 https://doi.org/10.1016/s0040-4020(99)00201-x Zobrazit plný text záznamu Full Text from ScienceDirect