ASPECTS OF THE ADDITION OF IODINE(I) AZIDE TO ALKENES

被引:11
作者
CAMBIE, RC
HAYWARD, RC
RUTLEDGE, PS
SMITHPALMER, T
SWEDLUND, BE
WOODGATE, PD
机构
[1] Department of Chemistry, University of Auckland, Auckland
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 01期
关键词
D O I
10.1039/p19790000180
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iodine(I) azide, formed from sodium azide-iodine(I) chloride, exists in acetonitrile as a complex with sodium azide. Addition of iodine(I) azide to cyclohexene gives a cis-iodo-azide as well as the expected trans-adduct. The addition of iodine(I) azide to a mixture of (Z)- and (E)-[β- 2H]styrene occurs in a stereospecific manner. In contrast to a literature report, the addition of iodine(I) azide to 1-methylcyclohexene is faster than to cyclohexene. intermediates in these reactions are discussed.
引用
收藏
页码:180 / 184
页数:5
相关论文
共 21 条
[1]   A SPECTROPHOTOMETRIC STUDY OF IODINE CHLORIDE IN VARIOUS SOLVENTS [J].
BUCKLES, RE ;
MILLS, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (19) :4845-4849
[2]   REACTIONS OF THALLIUM(I) AZIDE AND IODINE WITH ALKENES [J].
CAMBIE, RC ;
HAYWARD, RC ;
RUTLEDGE, PS ;
SMITHPALMER, T ;
WOODGATE, PD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (08) :840-845
[3]   PREVOST REACTION WITH 5ALPHA-ANDROST-2-ENE [J].
CAMBIE, RC ;
POTTER, GJ ;
RUTLEDGE, PS ;
WOODGATE, PD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (05) :530-537
[4]   REACTIONS OF THALLIUM(I) CARBOXYLATES AND IODINE WITH ALKENES [J].
CAMBIE, RC ;
HAYWARD, RC ;
ROBERTS, JL ;
RUTLEDGE, PS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (15) :1858-1864
[5]   IODO-AZIDE ADDUCTS OF 3-METHYL-DELTA-2-STEROIDS - STRUCTURE AND SOLVOLYSIS [J].
CAMBIE, RC ;
RUTLEDGE, PS ;
SMITHPALMER, T ;
WOODGATE, PD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (20) :2250-2257
[6]  
CAMBIE RC, 1977, JCS P1, P222
[7]   ISOLATION AND INFRARED-SPECTRUM OF IODINE AZIDE [J].
DEHNICKE, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (09) :553-554
[8]  
DELAMARE PBD, 1976, ELECTROPHILIC HALOGE, P174
[9]  
DUBOIS JE, 1964, TETRAHEDRON LETT, P2167
[10]  
DUBOIS JE, 1965, TETRAHEDRON LETT, P1217