Autoxidation of acridanyl and benzhydryl carbanions adjacent to sulfur groups leading to C-S bond cleavage with weak chemiluminescence

Jiro Motoyoshiya, Hisashi Inoue, Yutaka Takaguchi, Hiromu Aoyama

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Abstract

Autoxidation of acridanyl and benzhydryl carbanions stabilized by sulfur groups gave the corresponding ketones via radical intermediates, being accompanied by a weak light emission. While oxidation of 9-sulfenylacridanes (1a and 1b) in the presence of tert-BuOK showed direct chemiluminescence (CL) due to excited 10-methylacridone, that of benzhydryl phenyl sulfide (2) and benzhydryldimethyl-sulfomium bromide (3) displayed CL in the presence of a fluorescer, 9, 10-dibromoanthracene (DBA), due to excited benzophenone. The yields of excited species in the present oxidation are low but comparable to acyclic peroxide systems. The bimolecular energy transfer from triplet benzophenone to DBA was established in CL of the sulfonium ylide from 3.

Original languageEnglish
Pages (from-to)252-257
Number of pages6
JournalHeteroatom Chemistry
Volume13
Issue number3
DOIs
Publication statusPublished - 2002
Externally publishedYes

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ASJC Scopus subject areas

  • Chemistry(all)

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