Radical azidonation of aldehydes

被引:83
作者
Marinescu, L [1 ]
Thinggaard, J [1 ]
Thomsen, IB [1 ]
Bols, M [1 ]
机构
[1] Aarhus Univ, Dept Chem, DK-8000 Aarhus C, Denmark
关键词
D O I
10.1021/jo035163v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aliphatic and aromatic aldehydes can be converted to acyl azides by treatment with iodine azide at 0-25 degreesC. If the reaction is performed at reflux Curtius rearrangement occurs and carbamoyl azides are obtained in 70-97% yield from the aldehyde. The reaction was shown to have a radical mechanism.
引用
收藏
页码:9453 / 9455
页数:3
相关论文
共 18 条
[1]   DIRECT CONVERSION OF CARBOXYLIC-ACIDS INTO CARBAMOYL AZIDES [J].
AFFANDI, H ;
BAYQUEN, AV ;
READ, RW .
TETRAHEDRON LETTERS, 1994, 35 (17) :2729-2732
[2]  
ALLEN CFH, ORGANIC SYNTHESIS, V3, P846
[3]   An azido-hanessian reaction [J].
Baruah, M ;
Bols, M .
SYNLETT, 2002, (07) :1111-1112
[4]   IODO-AZIDE ADDUCTS OF EXOCYCLIC ALKENES - STRUCTURE AND SOLVOLYSIS [J].
CAMBIE, RC ;
JURLINA, JL ;
RUTLEDGE, PS ;
WOODGATE, PD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (02) :315-325
[6]   A NOVEL AND MILD SOURCE OF CARBON-CENTERED RADICALS BY IODOSOBENZENE DIACETATE (IBDA) AND SODIUM-AZIDE FROM ALCOHOLS, ETHERS, ALDEHYDES, AMIDES AND ALKYL IODIDES [J].
FONTANA, F ;
MINISCI, F ;
YAN, YM ;
ZHAO, LH .
TETRAHEDRON LETTERS, 1993, 34 (15) :2517-2520
[7]   OXIDATION OF ALDEHYDES TO ACYL AZIDES BY CHROMIC ANHYDRIDE-AZIDOTRIMETHYLSILANE [J].
LEE, JG ;
KWAK, KH .
TETRAHEDRON LETTERS, 1992, 33 (22) :3165-3166
[8]   CARBAMOYL AZIDES [J].
LIEBER, E ;
MINNIS, RL ;
RAO, CNR .
CHEMICAL REVIEWS, 1965, 65 (03) :377-&
[9]   DIRECT N-ALKYL AZIDONATION OF N,N-DIALKYLARYLAMINES WITH THE IODOSYLBENZENE TRIMETHYLSILYLAZIDE REAGENT COMBINATION [J].
MAGNUS, P ;
LACOUR, J ;
WEBER, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (20) :9347-9348
[10]   PHOSPHORUS IN ORGANIC SYNTHESIS .7. DIPHENYL PHOSPHORAZIDATE (DPPA) - NEW CONVENIENT REAGENT FOR A MODIFIED CURTIUS REACTION [J].
NINOMIYA, K ;
SHIOIRI, T ;
YAMADA, S .
TETRAHEDRON, 1974, 30 (14) :2151-2157