期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 69, 期 24, 页码 8177-8182出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo0490346
关键词
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Dibenzothiophene-5-oxide (DBTO) cleanly produces dibenzothiophene (DBT) on direct photolysis, but with very low quantum yield. A proposed mechanism involves scission of the S-O bond which is coupled to an intersystem crossing step, thus producing the sulfide and O((3)p) via a unimolecular pathway. To test this hypothesis, heavy atom substituted DBTOs were prepared and photolyzed. lodo-, bromo-, and chloro-substituted DBTOs show higher quantum yields for deoxygenation than does the parent molecule, in the order consistent with an intersystem crossing-related heavy atom effect. 2-lododibenzothiophene also undergoes photochemical deiodination. Phosphorescence data are consistent with heavy-atom assisted intersystem crossing.
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