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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 24期

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

[5] OXIDATION OF ALDEHYDES TO ACYL AZIDES USING TRIAZIDOCHLOROSILANE (TACS)-ACTIVE MANGANESE-DIOXIDE REAGENT [J].

ELMORSY, SS .

TETRAHEDRON LETTERS, 1995, 36 (08) :1341-1342

[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