SOME BY-PRODUCTS IN THE S(E)2' REACTIONS OF AN ALLENYLSILANE WITH ALDEHYDES

被引:18
作者
ARCHIBALD, SC [1 ]
FLEMING, I [1 ]
机构
[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)77621-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction between the allenylsilane 1 and isobutyraldehyde 2 gives a minor byproduct 7, and the reaction between the allenylsilane 1 and the aldehyde 14 gives a succession of products 16, 18, and 19 arising from the phenyl group attacking the aldehyde intramolecularly faster than the allenylsilane can attack it.
引用
收藏
页码:2387 / 2390
页数:4
相关论文
共 11 条
[1]  
ANH NT, 1977, NOUV J CHIM, V1, P61
[2]   CATION EXCHANGE RESIN-CATALYZED CONDENSATION AND POLYMERIZATION OF ALDEHYDES AND CYCLOHEXANONE [J].
ASTLE, MJ ;
PINNS, ML .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (01) :56-60
[3]   ACCURATE DETERMINATION OF THE EXTENT TO WHICH THE S(E)2' REACTIONS OF AN ALLENYLSILANE ARE STEREOSPECIFICALLY ANTI [J].
BUCKLE, MJC ;
FLEMING, I .
TETRAHEDRON LETTERS, 1993, 34 (14) :2383-2386
[4]  
CHEREST M, 1968, TETRAHEDRON LETT, P2199
[5]   THE DIASTEREOSELECTIVITY OF ELECTROPHILIC ATTACK ON TRIGONAL CARBON ADJACENT TO A STEREOGENIC CENTER - DIASTEREOSELECTIVE ALKYLATION AND PROTONATION OF OPEN-CHAIN ENOLATES HAVING A STEREOGENIC CENTER CARRYING A SILYL GROUP AT THE BETA POSITION [J].
CRUMP, RANC ;
FLEMING, I ;
HILL, JHM ;
PARKER, D ;
REDDY, NL ;
WATERSON, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (24) :3277-3294
[6]  
DENMARK SE, 1992, TETRAHEDRON, V48, P5565
[7]   STEREOCONTROL IN ORGANIC-SYNTHESIS USING SILICON-COMPOUNDS [J].
FLEMING, I .
PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :1879-1886
[8]   CARBONIUM-ION REARRANGEMENTS CONTROLLED BY THE PRESENCE OF A SILYL GROUP [J].
FLEMING, I ;
PATEL, SK ;
URCH, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01) :115-124
[9]   A ONE-POT CONVERSION OF THE PHENYLDIMETHYLSILYL GROUP INTO A HYDROXYL GROUP [J].
FLEMING, I ;
SANDERSON, PEJ .
TETRAHEDRON LETTERS, 1987, 28 (36) :4229-4232
[10]   THE PHENYLDIMETHYLSILYL GROUP AS A MASKED FORM OF THE HYDROXY GROUP [J].
FLEMING, I ;
HENNING, R ;
PLAUT, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (01) :29-31