Synthesis and reactivity of dipropargylic disulfides: tandem rearrangements, cyclization, and oxidative dimerization

Samuel Braverman; Marina Cherkinsky; David Meridor; Milon Sprecher

doi:10.1016/j.tet.2010.01.012

Synthesis and reactivity of dipropargylic disulfides: tandem rearrangements, cyclization, and oxidative dimerization

Samuel Braverman
, Marina Cherkinsky
, David Meridor
, Milon Sprecher

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

11 Scopus citations

Abstract

Synthesis and facile rearrangement and cyclization reaction of new dipropargylic disulfides are described. A possible mechanism for these transformations involving an initial double [2,3]-sigmatropic rearrangement to the elusive diallenyl disulfides via a thiosulfoxide intermediates is suggested.

Original language	English
Pages (from-to)	1925-1930
Number of pages	6
Journal	Tetrahedron
Volume	66
Issue number	10
DOIs	https://doi.org/10.1016/j.tet.2010.01.012
State	Published - 6 Mar 2010
Externally published	Yes

Keywords

Desulfurization
Disulfides
Sigmatropic rearrangement
Thioethers
Thiols
Thiosulfates
Thiosulfoxides

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2010.01.012

Cite this

@article{d20be9be8d974f688b8b090ac5505508,

title = "Synthesis and reactivity of dipropargylic disulfides: tandem rearrangements, cyclization, and oxidative dimerization",

abstract = "Synthesis and facile rearrangement and cyclization reaction of new dipropargylic disulfides are described. A possible mechanism for these transformations involving an initial double [2,3]-sigmatropic rearrangement to the elusive diallenyl disulfides via a thiosulfoxide intermediates is suggested.",

keywords = "Desulfurization, Disulfides, Sigmatropic rearrangement, Thioethers, Thiols, Thiosulfates, Thiosulfoxides",

author = "Samuel Braverman and Marina Cherkinsky and David Meridor and Milon Sprecher",

year = "2010",

month = mar,

day = "6",

doi = "10.1016/j.tet.2010.01.012",

language = "English",

volume = "66",

pages = "1925--1930",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "10",

}

TY - JOUR

T1 - Synthesis and reactivity of dipropargylic disulfides

T2 - tandem rearrangements, cyclization, and oxidative dimerization

AU - Braverman, Samuel

AU - Cherkinsky, Marina

AU - Meridor, David

AU - Sprecher, Milon

PY - 2010/3/6

Y1 - 2010/3/6

N2 - Synthesis and facile rearrangement and cyclization reaction of new dipropargylic disulfides are described. A possible mechanism for these transformations involving an initial double [2,3]-sigmatropic rearrangement to the elusive diallenyl disulfides via a thiosulfoxide intermediates is suggested.

AB - Synthesis and facile rearrangement and cyclization reaction of new dipropargylic disulfides are described. A possible mechanism for these transformations involving an initial double [2,3]-sigmatropic rearrangement to the elusive diallenyl disulfides via a thiosulfoxide intermediates is suggested.

KW - Desulfurization

KW - Disulfides

KW - Sigmatropic rearrangement

KW - Thioethers

KW - Thiols

KW - Thiosulfates

KW - Thiosulfoxides

UR - https://www.scopus.com/pages/publications/75849151751

U2 - 10.1016/j.tet.2010.01.012

DO - 10.1016/j.tet.2010.01.012

M3 - Article

AN - SCOPUS:75849151751

SN - 0040-4020

VL - 66

SP - 1925

EP - 1930

JO - Tetrahedron

JF - Tetrahedron

IS - 10

ER -

Synthesis and reactivity of dipropargylic disulfides: tandem rearrangements, cyclization, and oxidative dimerization

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this