Novel route to triethylsilyl-substituted cyclopropanes

Shi Guang Li; Samir Z. Zard

doi:10.1021/ol503081b

Novel route to triethylsilyl-substituted cyclopropanes

Shi Guang Li, Samir Z. Zard

Laboratoire de Synthèse Organique

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

Abstract

Radical adducts of S-α-ketonyl dithiocarbonates (xanthates) to triethyl vinylsilane are converted into triethylsilyl-substituted cyclopropanes upon ozonolysis followed by exposure to 1,4-dibromobutane and Cs₂CO₃/18-crown-6 in refluxing acetonitrile. The sequence works best with phenacyl type adducts, and the use of the less bulky trimethysilyl (TMS) derivatives results in extensive desilylation.

Original language	English
Pages (from-to)	6180-6183
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	23
DOIs	https://doi.org/10.1021/ol503081b
Publication status	Published - 5 Dec 2014
Externally published	Yes

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title = "Novel route to triethylsilyl-substituted cyclopropanes",

abstract = "Radical adducts of S-α-ketonyl dithiocarbonates (xanthates) to triethyl vinylsilane are converted into triethylsilyl-substituted cyclopropanes upon ozonolysis followed by exposure to 1,4-dibromobutane and Cs2CO3/18-crown-6 in refluxing acetonitrile. The sequence works best with phenacyl type adducts, and the use of the less bulky trimethysilyl (TMS) derivatives results in extensive desilylation.",

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doi = "10.1021/ol503081b",

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AU - Li, Shi Guang

AU - Zard, Samir Z.

PY - 2014/12/5

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N2 - Radical adducts of S-α-ketonyl dithiocarbonates (xanthates) to triethyl vinylsilane are converted into triethylsilyl-substituted cyclopropanes upon ozonolysis followed by exposure to 1,4-dibromobutane and Cs2CO3/18-crown-6 in refluxing acetonitrile. The sequence works best with phenacyl type adducts, and the use of the less bulky trimethysilyl (TMS) derivatives results in extensive desilylation.

AB - Radical adducts of S-α-ketonyl dithiocarbonates (xanthates) to triethyl vinylsilane are converted into triethylsilyl-substituted cyclopropanes upon ozonolysis followed by exposure to 1,4-dibromobutane and Cs2CO3/18-crown-6 in refluxing acetonitrile. The sequence works best with phenacyl type adducts, and the use of the less bulky trimethysilyl (TMS) derivatives results in extensive desilylation.

U2 - 10.1021/ol503081b

DO - 10.1021/ol503081b

M3 - Article

AN - SCOPUS:84916217706

SN - 1523-7060

VL - 16

SP - 6180

EP - 6183

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Novel route to triethylsilyl-substituted cyclopropanes

Abstract

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