A synthesis of (1 E,3 E)-TMS dienes from keto-xanthates via Chugaev-type elimination

Kelvin Kau Kiat Goh; Sunggak Kim; Samir Z. Zard

doi:10.1021/jo402169v

A synthesis of (1 E,3 E)-TMS dienes from keto-xanthates via Chugaev-type elimination

Kelvin Kau Kiat Goh
, Sunggak Kim
, Samir Z. Zard

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

Abstract

An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.

Original language	English
Pages (from-to)	12274-12279
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	78
Issue number	23
DOIs	https://doi.org/10.1021/jo402169v
Publication status	Published - 6 Dec 2013
Externally published	Yes

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10.1021/jo402169v

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title = "A synthesis of (1 E,3 E)-TMS dienes from keto-xanthates via Chugaev-type elimination",

abstract = "An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.",

author = "Goh, \{Kelvin Kau Kiat\} and Sunggak Kim and Zard, \{Samir Z.\}",

year = "2013",

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doi = "10.1021/jo402169v",

language = "English",

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pages = "12274--12279",

journal = "Journal of Organic Chemistry",

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T1 - A synthesis of (1 E,3 E)-TMS dienes from keto-xanthates via Chugaev-type elimination

AU - Goh, Kelvin Kau Kiat

AU - Kim, Sunggak

AU - Zard, Samir Z.

PY - 2013/12/6

Y1 - 2013/12/6

N2 - An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.

AB - An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.

U2 - 10.1021/jo402169v

DO - 10.1021/jo402169v

M3 - Article

AN - SCOPUS:84890164709

SN - 0022-3263

VL - 78

SP - 12274

EP - 12279

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

A synthesis of (1 E,3 E)-TMS dienes from keto-xanthates via Chugaev-type elimination

Abstract

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