CATIONIC CARBON TO NITROGEN REARRANGEMENTS IN THE REACTIONS OF N-(SULFONYLOXY)AMINES WITH ALDEHYDES

被引:12
作者
HOFFMAN, RV
SALVADOR, JM
机构
[1] Department of Chemistry, New Mexico State University, Las Cruces
关键词
D O I
10.1021/jo00042a032
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of aromatic and aliphatic aldehydes was reacted with N-((p-nitrobenzenesulfonyl)oxy)methylamine in chloroform. Products resulting from both carbon migration and hydride migration to nitrogen were isolated. The ratios of carbon to hydride migration products were used to clarify the reaction mechanism. The results support a two-step process in which cationic carbon to nitrogen rearrangement is rate determining.
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收藏
页码:4487 / 4490
页数:4
相关论文
共 35 条
[1]   INTRAMOLECULAR SCHMIDT REACTION OF ALKYL AZIDES [J].
AUBE, J ;
MILLIGAN, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8965-8966
[2]   SUBSTITUENT EFFECTS ON THE H-1 NMR-SPECTRA OF SUBSTITUTED BENZAMIDES AND N-ALKYLBENZAMIDES [J].
CALVERT, DJ ;
OCONNOR, J .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (02) :337-343
[3]   BIOSYNTHESIS OF ASPYRONE, A METABOLITE OF ASPERGILLUS-MELLEUS - INCORPORATION STUDIES WITH C-14-LABELED AND H-3-LABELED ACETATES AND MALONATE [J].
COPELAND, RJ ;
HILL, RA ;
HINCHCLIFFE, DJ ;
STAUNTON, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :1013-1019
[4]  
DIMAIO G, 1966, TETRAHEDRON, V22, P2059
[5]   EFFECTS OF ACID STRENGTH ON SCHMIDT REACTIONS OF ALKYL CYCLOPROPYL KETONES AND ALKYL PHENYL KETONES [J].
FIKES, LE ;
SHECHTER, H .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (05) :741-744
[6]   SPECTROSCOPIC STUDY OF MONOSUBSTITUTED AMIDES .2. ROTATION ISOMERS IN AMIDES SUBSTITUTED BY ALIPHATIC SIDE-CHAIN MODELS [J].
FILLAUX, F ;
LOZE, CD .
BIOPOLYMERS, 1972, 11 (10) :2063-&
[7]   NUCLEAR MAGNETIC RESONANCE SPECTRA OF SOME N-MONOSUBSTITUTED METHYLAMINES [J].
FREIFELD.M ;
MATTOON, RW ;
KRIESE, R .
JOURNAL OF PHYSICAL CHEMISTRY, 1965, 69 (10) :3645-&
[8]  
GAJDA T, 1979, SYNTHESIS-STUTTGART, V7, P549
[9]   CATIONIC CARBON-TO-NITROGEN REARRANGEMENTS IN N-(ARYLSULFONOXY)AMINES [J].
HOFFMAN, RV ;
KUMAR, A .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (11) :1859-1863
[10]   ADDITION-REARRANGEMENT REACTIONS OF N-(ARYLSULFONYLOXY)AMINES AND 3,4-DIHYDRO-2H-PYRAN [J].
HOFFMAN, RV ;
SALVADOR, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08) :1375-1380