Radical allylation of trifluoromethylated xanthates: use of DEAD for removing the allyltributyltin excess

被引：12

作者：

Blazejewski, JC ^{[1
]}

Diter, P ^{[1
]}

Warchol, T ^{[1
]}

Wakselman, C ^{[1
]}

机构：

[1] Univ Versailles, SIRCOB, ESA CNRS 8086, F-78035 Versailles, France

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(00)02135-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Radical allylation of trifluoromethylated xanthates allows the preparation of quaternary carbon centers bearing the trifluoromethyl group. An excess of the allyltributyltin reagent must be used in order to achieve satisfactory yields of the adducts. The excess of reagent could be conveniently removed by the use of diethylazodicarboxylate (DEAD). (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：859 / 861

页数：3

共 36 条

[1] ABELE H, 1993, J FLOURINE CHEM, V40, P2319
[2] ABSOLUTE RATE CONSTANTS FOR SOME REACTIONS OF PERFLUORO-N-ALKYL RADICALS IN SOLUTION
AVILA, DV
INGOLD, KU
LUSZTYK, J
DOLBIER, WR
PAN, HQ
MUIR, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (01) : 99 - 104
[3] ON THE STABILITY AND RADICAL DEOXYGENATION OF TERTIARY XANTHATES
BARTON, DHR
PAREKH, SI
TSE, CL
[J]. TETRAHEDRON LETTERS, 1993, 34 (17) : 2733 - 2736
[4] BEGUE JP, 1991, SYNLETT, P146
[5] THE ANGULAR TRIFLUOROMETHYL GROUP .1. TOTAL SYNTHESIS OF 13-TRIFLUOROMETHYL ESTROGENS
BLAZEJEWSKI, JC
DORME, R
WAKSELMAN, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (02): : 337 - 341
[6] THE ANGULAR TRIFLUOROMETHYL GROUP .2. SYNTHESIS OF (+)2,3,7,7A-TETRAHYDRO-7A-TRIFLUOROMETHYL-1H-INDENE-1,5-(6H)-DIONE
BLAZEJEWSKI, JC
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1990, 46 (03) : 515 - 519
[7] THE ANGULAR TRIFLUOROMETHYL GROUP .4. SYNTHESIS OF THE 9,9,9-TRIFLUORO ANALOG OF THE WIELAND-MIESCHER KETONE
BLAZEJEWSKI, JC
LEGUYADER, F
WAKSELMAN, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05): : 1121 - 1125
[8] THE ANGULAR TRIFLUOROMETHYL GROUP .3. SYNTHESIS OF A RING-D PRECURSOR OF TRIFLUOROMETHYLATED STEROIDS
BLAZEJEWSKI, JC
HADDAD, M
WAKSELMAN, C
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1991, 52 (03) : 353 - 360
[9] Short stereoselective route to γ-CF3 allylic alcohols:: Rearrangements with creation of quaternary CF3-substituted carbons
Bouvet, D
Sdassi, H
Ourévitch, M
Bonnet-Delpon, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) : 2104 - 2107
[10] COMPARATIVE-STUDIES ON THE GENERATION AND CYCLIZATION REACTIONS OF DIFLUOROALKYL RADICALS
BUTTLE, LA
MOTHERWELL, WB
[J]. TETRAHEDRON LETTERS, 1994, 35 (23) : 3995 - 3998

← 1 2 3 4 →