2,7-Di-tert-butylnaphtho[1,8-cd][1,2]dithiole 1,2-dioxides: thermally stable, photochemically active vic-disulfoxides

Richard S. Grainger; Bhaven Patel; Benson M. Kariuki

doi:10.1002/anie.200901788

2,7-Di-tert-butylnaphtho[1,8-cd][1,2]dithiole 1,2-dioxides: thermally stable, photochemically active vic-disulfoxides

Richard S. Grainger
, Bhaven Patel
, Benson M. Kariuki

Chemistry

Research output: Contribution to journal › Article

25 Citations (Scopus)

Abstract

Bulking up: The thermal barrier to rearrangement of a vic-disulfoxide is significantly increased through steric buttressing about the (O)S--S(O) bond. Whereas the title compounds represent the most thermally stable vic-disulfoxides known to date, they also undergo a novel photomediated epimerization at room temperature (see scheme).

Original language	English
Pages (from-to)	4832-4835
Number of pages	4
Journal	Angewandte Chemie (International Edition)
Volume	48
Issue number	26
DOIs	https://doi.org/10.1002/anie.200901788
Publication status	Published - 9 Jun 2009

Keywords

isomerization
oxidation
rearrangement
sulfur heterocycles
substituent effects

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10.1002/anie.200901788Licence: None: All rights reserved

Harnessing Reactive Intermediates for Organic Synthesis
Grainger, R. (Principal Investigator)
Engineering & Physical Science Research Council
1/10/05 → 31/03/09
Project: Research Councils
Advanced Research Fellowship: Harnessing Reactive Intermediates for Organic Synthesis
Grainger, R. (Principal Investigator)
Engineering & Physical Science Research Council
1/09/05 → 31/08/10
Project: Research Councils

Cite this

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title = "2,7-Di-tert-butylnaphtho[1,8-cd][1,2]dithiole 1,2-dioxides: thermally stable, photochemically active vic-disulfoxides",

abstract = "Bulking up: The thermal barrier to rearrangement of a vic-disulfoxide is significantly increased through steric buttressing about the (O)S--S(O) bond. Whereas the title compounds represent the most thermally stable vic-disulfoxides known to date, they also undergo a novel photomediated epimerization at room temperature (see scheme).",

keywords = "isomerization, oxidation, rearrangement, sulfur heterocycles, substituent effects",

author = "Grainger, \{Richard S.\} and Bhaven Patel and Kariuki, \{Benson M.\}",

year = "2009",

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doi = "10.1002/anie.200901788",

language = "English",

volume = "48",

pages = "4832--4835",

journal = "Angewandte Chemie (International Edition) ",

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publisher = "Wiley-VCH Verlag",

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T1 - 2,7-Di-tert-butylnaphtho[1,8-cd][1,2]dithiole 1,2-dioxides

T2 - thermally stable, photochemically active vic-disulfoxides

AU - Grainger, Richard S.

AU - Patel, Bhaven

AU - Kariuki, Benson M.

PY - 2009/6/9

Y1 - 2009/6/9

N2 - Bulking up: The thermal barrier to rearrangement of a vic-disulfoxide is significantly increased through steric buttressing about the (O)S--S(O) bond. Whereas the title compounds represent the most thermally stable vic-disulfoxides known to date, they also undergo a novel photomediated epimerization at room temperature (see scheme).

AB - Bulking up: The thermal barrier to rearrangement of a vic-disulfoxide is significantly increased through steric buttressing about the (O)S--S(O) bond. Whereas the title compounds represent the most thermally stable vic-disulfoxides known to date, they also undergo a novel photomediated epimerization at room temperature (see scheme).

KW - isomerization

KW - oxidation

KW - rearrangement

KW - sulfur heterocycles

KW - substituent effects

UR - https://publons.com/publon/8189752/

U2 - 10.1002/anie.200901788

DO - 10.1002/anie.200901788

M3 - Article

C2 - 19475586

SN - 1521-3773

VL - 48

SP - 4832

EP - 4835

JO - Angewandte Chemie (International Edition)

JF - Angewandte Chemie (International Edition)

IS - 26

ER -

2,7-Di-tert-butylnaphtho[1,8-cd][1,2]dithiole 1,2-dioxides: thermally stable, photochemically active vic-disulfoxides

Abstract

Keywords

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Projects

Harnessing Reactive Intermediates for Organic Synthesis

Advanced Research Fellowship: Harnessing Reactive Intermediates for Organic Synthesis

Cite this