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

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

6 Citations (Scopus)

Résumé

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.

langue originale	Anglais
Pages (de - à)	6180-6183
Nombre de pages	4
journal	Organic Letters
Volume	16
Numéro de publication	23
Les DOIs	https://doi.org/10.1021/ol503081b
état	Publié - 5 déc. 2014
Modification externe	Oui

Accès au document

10.1021/ol503081b

Contient cette citation

@article{0df8c0970dc74a51a33139237b3912cd,

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.",

author = "Li, \{Shi Guang\} and Zard, \{Samir Z.\}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

month = dec,

day = "5",

doi = "10.1021/ol503081b",

language = "English",

volume = "16",

pages = "6180--6183",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - Novel route to triethylsilyl-substituted cyclopropanes

AU - Li, Shi Guang

AU - Zard, Samir Z.

PY - 2014/12/5

Y1 - 2014/12/5

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

Résumé

Accès au document

Empreinte digitale

Contient cette citation