STEREOELECTRONIC EFFECTS IN THE CONFORMATIONAL BEHAVIOR AND RING FORMATION OF SOME N,N'-DIMETHYL-1,5-DIOXA-4,8-DIAZADECALINS AND N,N'-DIACETYL-1,5-DIOXA-4,8-DIAZADECALINS

被引：8
作者：
ALCAIDE, B [1 ]
JIMENEZBARBERO, J [1 ]
PLUMET, J [1 ]
RODRIGUEZCAMPOS, IM [1 ]
机构：
[1] CSIC,INST QUIM ORGAN GEN,E-28006 MADRID,SPAIN
来源：
TETRAHEDRON | 1992年 / 48卷 / 13期
关键词：
D O I：
10.1016/S0040-4020(01)88531-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of 4,8-dimethyl- and 4,8-diacetyl-cis-octahydro-[1,4]oxazino[3,2-b]-1,4-oxazines (title compounds) 4 and 7 respectively, were synthesized and studied using H-1- and C-13-NMR techniques. Conformational analysis of 4 showed a strong preference for conformers possessing an anti-N/gauche-O array vs an anti-O/gauche-N relationship (DELTA-G(O) = 0.88 Kcal/mol). However 7b exists exclusively as an anti-O/gauche-N conformer with a free energy of activation for the amide rotation barrier of 11.6 Kcal/mol (248 K). The stereoelectronic features of the C-N-C-O-C moieties of 4 and 7 are emphasized. A general reaction pathway is also discussed.
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页码：2715 / 2728
页数：14
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