Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

10-26-2004

Journal or Book Title

The Journal of Organic Chemistry

Volume

69

Issue

24

First Page

8177

Last Page

8182

DOI

10.1021/jo0490346

Abstract

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(3P) via a unimolecular pathway. To test this hypothesis, heavy atom substituted DBTOs were prepared and photolyzed. Iodo-, 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-Iododibenzothiophene also undergoes photochemical deiodination. Phosphorescence data are consistent with heavy-atom assisted intersystem crossing.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 2004 69(24); 8177-8182. DOI: 10.1021/jo0490346. Copyright 2004 American Chemical Society.

Rights

One-time permission is granted only for the use specified in your request. No additional uses are granted (such as derivative works or other editions). For any other uses, please submit a new request.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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