TRIETHYLBORANE INDUCED RADICAL REACTION OF KETENE SILYL ACETALS WITH POLYHALOMETHANES - SYNTHESIS OF 3,3-DIHALOACRYLATES AND 3-HALOACRYLATES

被引：13

作者：

SUGIMOTO, J

MIURA, K

OSHIMA, K

UTIMOTO, K

机构：

来源：

CHEMISTRY LETTERS | 1991年 / 08期

关键词：

D O I：

10.1246/cl.1991.1319

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of ketene octyl t-butyldimethylsilyl acetal with tetrabromomethane or tribromomethane in the presence of a catalytic amount of triethylborane gave octyl 3,3-dibromoacrylate or octyl (E)-3-bromoacrylate, respectively.

引用

页码：1319 / 1322

页数：4

共 44 条

[1] TRIETHYLBORANE INDUCED RADICAL REACTION OF KETENE SILYL ACETALS WITH POLYHALOMETHANES
MIURA, K
SUGIMOTO, J
OSHIMA, K
UTIMOTO, K
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (06) : 1513 - 1521
[2] Reaction of peroxyacetals with silyl ketene acetals: synthesis of 3-peroxyalkanoates and 3-peroxyalkanals
Dussault, PH
Lee, RJ
Schultz, JA
Suh, YS
TETRAHEDRON LETTERS, 2000, 41 (29) : 5457 - 5460
[3] Chiral silyl ketene acetals from thioesters: Reaction with acetals and peroxyacetals to form 3-alkoxy- and 3-peroxyalkanoates
Dussault, PH
Trullinger, TK
Cho-Shultz, S
TETRAHEDRON, 2000, 56 (47) : 9213 - 9220
[4] SYNTHESIS VIA SIGMATROPIC REARRANGEMENTS .11. [3,3]-SIGMATROPIC REARRANGEMENT OF SILYL KETENE ACETALS OF METHYL ALPHA-(ALLYLOXY)ACETATES
RAUCHER, S
GUSTAVSON, LM
TETRAHEDRON LETTERS, 1986, 27 (14) : 1557 - 1560
[5] Tandem Insertion/[3,3]-Sigmatropic Rearrangement Involving the Formation of Silyl Ketene Acetals by Insertion of Rhodium Carbenes into S-Si Bonds
Combs, Jason R.
Lai, Yin-Chu
Van Vranken, David L.
ORGANIC LETTERS, 2021, 23 (08) : 2841 - 2845
[6] Sakurai Reaction of 3,3-Bis(silyl) Silyl Enol Ethers with Acetals Involving Selective Desilylation of the Geminal Bis(silane). Concise Synthesis of Nematocidal Oxylipid
Li, Linjie
Ye, Xincui
Wu, Ya
Gao, Lu
Song, Zhenlei
Yin, Zhiping
Xu, Yongjin
ORGANIC LETTERS, 2013, 15 (05) : 1068 - 1071
[7] Vicinal alkylation-carboxymethylation of electron-poor alkenes by radical-chain reactions with O-alkyl O-silyl ketene acetals and their [3+2] annulation by reaction with O-cyclopropylcarbinyl O-silyl ketene acetals
Cai, YD
Roberts, BP
TETRAHEDRON LETTERS, 2004, 45 (07) : 1485 - 1488
[8] ELECTROPHILIC SULFENYLATION OF SILYL KETENE ACETALS DERIVED FROM 3-HYDROXY-ESTERS - DIASTEREOSELECTIVE SYNTHESIS OF PROTECTED EPOXYALCOHOLS
GUANTI, G
BANFI, L
NARISANO, E
THEA, S
CHEMISTRY LETTERS, 1988, (10) : 1683 - 1686
[9] TRIFLUOROMETHANESULFONIC ACID-PROMOTED REACTION OF HEXAHYDRO-1,3,5-TRIAZINES WITH KETENE SILYL ACETALS - CONVENIENT SYNTHESIS OF ALKYL BETA-AMINOCARBOXYLATES
IKEDA, K
ACHIWA, K
SEKIYA, M
TETRAHEDRON LETTERS, 1983, 24 (09) : 913 - 916
[10] Regioselective formation of 3-selanyl-3-siloxyoxetanes in the Paternò - Büchi reaction of silyl O,Se-ketene acetals (O,Se-SKA)
Abe, M. (abe@ap.chem.eng.osaka-u.ac.jp), 2001, Georg Thieme Verlag

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