Beckmann rearrangement of oximes under very mild conditions

被引:195
作者
De Luca, L [1 ]
Giacomelli, G [1 ]
Porcheddu, A [1 ]
机构
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
关键词
D O I
10.1021/jo025960d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of ketoximes, easily prepared from the corresponding ketones, undergo the Beckmann rearrangement upon treatment with 2,4,6-trichloro[1,3,5]triazine in N,N-dimethylformamide at room temperature in excellent yields. This procedure can be applied to aldoximes for obtaining the corresponding nitriles.
引用
收藏
页码:6272 / 6274
页数:3
相关论文
共 26 条
[1]   Improved procedures for the Beckmann rearrangement: the reaction of ketoxime carbonates with boron trifluoride etherate [J].
Anilkumar, R ;
Chandrasekhar, S .
TETRAHEDRON LETTERS, 2000, 41 (28) :5427-5429
[2]   Rhodium-catalyzed Beckmann rearrangement [J].
Arisawa, M ;
Yamaguchi, M .
ORGANIC LETTERS, 2001, 3 (02) :311-312
[3]   NEW ROUTE TO NITRILES - DEHYDRATION OF ALDOXIMES USING 2,4,6-TRICHLORO-S-TRIAZINE (CYANURIC CHLORIDE) [J].
CHAKRABARTI, JK ;
HOTTEN, TM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (22) :1226-+
[4]   An efficient route to alkyl chlorides from alcohols using the complex TCT/DMF [J].
De Luca, L ;
Giacomelli, G ;
Porcheddu, A .
ORGANIC LETTERS, 2002, 4 (04) :553-555
[5]   A mild and efficient alternative to the classical swern oxidation [J].
De Luca, L ;
Giacomelli, G ;
Porcheddu, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7907-7909
[6]   A very mild and chemoselective oxidation of alcohols to carbonyl compounds [J].
De Luca, L ;
Giacomelli, G ;
Porcheddu, A .
ORGANIC LETTERS, 2001, 3 (19) :3041-3043
[7]   An easy and convenient synthesis of Weinreb amides and hydroxamates [J].
De Luca, L ;
Giacomelli, G ;
Taddei, M .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07) :2534-2537
[8]   A simple preparation of ketones.: N-protected α-amino ketones from α-amino acids [J].
De Luca, L ;
Giacomelli, G ;
Porcheddu, A .
ORGANIC LETTERS, 2001, 3 (10) :1519-1521
[9]  
DELUCA L, 2002, IN PRESS J ORG CHEM, P67
[10]   NOVEL-APPROACH TO LACTAMS VIA (TRIISOPROPYLSILYL)AZIDOHYDRIN FORMATION AND PHOTOINDUCED SCHMIDT REARRANGEMENT [J].
EVANS, PA ;
MODI, DP .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6662-6663