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

doi:10.1002/hc.10025

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

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

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 language	English
Pages (from-to)	252-257
Number of pages	6
Journal	Heteroatom Chemistry
Volume	13
Issue number	3
DOIs	https://doi.org/10.1002/hc.10025
Publication status	Published - May 23 2002
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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

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.",

author = "Jiro Motoyoshiya and Hisashi Inoue and Yutaka Takaguchi and Hiromu Aoyama",

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T1 - Autoxidation of acridanyl and benzhydryl carbanions adjacent to sulfur groups leading to C-S bond cleavage with weak chemiluminescence

AU - Motoyoshiya, Jiro

AU - Inoue, Hisashi

AU - Takaguchi, Yutaka

AU - Aoyama, Hiromu

PY - 2002/5/23

Y1 - 2002/5/23

N2 - 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.

AB - 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.

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

Abstract

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