NEW METHOD FOR HOFMANN REARRANGEMENT

被引:31
作者
JEW, SS
PARK, HG
PARK, HJ
PARK, MS
CHO, YS
机构
[1] College of Pharmacy, Seoul National University, Seoul, 151-742, San 56-1, Shinrim-Dong, Kwanak-Ku
关键词
D O I
10.1016/0040-4039(90)80016-F
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of a series of primary aliphatic and aromatic carboxamides (la-lm) with NBS-Hg(OAc)2-R'OH (A), dibromantin-Hg(OAc)2-R'OH (B), NBS-AgOAc-R'OH (C), or dibromantin-AgOAc-R'OH (D) in DMF under argon provides corresponding carbamates (2a-2m) in nearly quantitative yields. © 1990.
引用
收藏
页码:1559 / 1562
页数:4
相关论文
共 24 条
[11]  
COOK C-H, 1984, Seoul University Journal of Pharmaceutical Sciences, V9, P44
[12]   A NEW CLASS OF AMINO-ACID BASED SWEETENERS [J].
FULLER, WD ;
GOODMAN, M ;
VERLANDER, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (20) :5821-5822
[13]   CONCEPT OF LINEAR MODIFIED RETRO-PEPTIDE STRUCTURES [J].
GOODMAN, M ;
CHOREV, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (01) :1-7
[14]   SODIUM BROMITE - A NEW REAGENT FOR THE HOFMANN DEGRADATION OF AMIDES [J].
KAJIGAESHI, S ;
NAKAGAWA, T ;
FUJISAKI, S ;
NISHIDA, A ;
NOGUCHI, M .
CHEMISTRY LETTERS, 1984, (05) :713-714
[15]   OXIDATION USING QUATERNARY AMMONIUM POLYHALIDES .1. AN EFFICIENT METHOD FOR THE HOFMANN DEGRADATION OF AMIDES BY USE OF BENZYLTRIMETHYLAMMONIUM TRIBROMIDE [J].
KAJIGAESHI, S ;
ASANO, K ;
FUJISAKI, S ;
KAKINAMI, T ;
OKAMOTO, T .
CHEMISTRY LETTERS, 1989, (03) :463-464
[16]  
KIZBER AI, 1953, ZH OBSHCH KHIM+, V23, P1028
[17]   DIRECT CONVERSION OF ALIPHATIC CARBOXAMIDES TO ALKYLAMMONIUM TOSYLATES WITH [HYDROXY(TOSYLOXY)IODO]BENZENE [J].
LAZBIN, IM ;
KOSER, GF .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2669-2671
[18]   CONVERSION OF ALIPHATIC AMIDES INTO AMINES WITH [I,I-BIS(TRIFLUOROACETOXY)IODO]BENZENE .1. SCOPE OF THE REACTION [J].
LOUDON, GM ;
RADHAKRISHNA, AS ;
ALMOND, MR ;
BLODGETT, JK ;
BOUTIN, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4272-4276
[19]  
MARCH J, 1985, ADV ORG CHEM, P983
[20]  
RADHAKRISHA AS, 1979, J ORG CHEM, V44, P1747