Sulfuration of 9,9 '-bibenzonorbornenylidenes by elemental sulfur: exclusive episulfide formation with retention of the configuration of alkenes | Health & Environmental Research Online (HERO)

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HERO ID

5249397

Reference Type

Journal Article

Title

Sulfuration of 9,9 '-bibenzonorbornenylidenes by elemental sulfur: exclusive episulfide formation with retention of the configuration of alkenes

Author(s)

Sugihara, Y; Noda, K; Nakayama, J

Year

2000

Is Peer Reviewed?

Journal

Tetrahedron Letters
ISSN: 0040-4039
EISSN: 1873-3581

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

Location

OXFORD

Volume

Issue

Page Numbers

8913-8916

Language

English

DOI

10.1016/s0040-4039(00)01605-1

Web of Science Id

WOS:000165398100015

URL

http:///www.elsevier.com
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Abstract

Sulfuration of syn-bibenzonorbornenylidene (5a) by elemental sulfur in refluxing o-dichlorobenzene furnished the episulfide (6a) exclusively in 83% yield with retention of the configuration of 5a, while that of anti-9,9'-bibenzonorbornenylidene (5b) under the same conditions resulted in the exclusive formation of the episulfide (6c) in 72% yield also with retention of the configuration of 5b. Non-stereoselective sulfuration of 5a and 5b by S(2)Cl(2) is also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

Keywords

Chemistry; Polymer Science; sulfuration, 9,9 '-bibenzonorbornenylidenes, episulfides,; stereochemistry, retention of configuration; electrophilic additions, pentathiepane ring, electronic control,; inversion barrier, stereoselectivity, conformers