SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF EXO-7-SUBSTITUTED-3-AZABICYCLO[3.3.1]NONANES AND ENDO-7-SUBSTITUTED-3-AZABICYCLO[3.3.1]NONANES

被引：21

作者：

BOK, TR ^{[1
]}

SPECKAMP, WN ^{[1
]}

机构：

[1] UNIV AMSTERDAM,ORGAN CHEM LAB,NL-1000 HE AMSTERDAM,NETHERLANDS

来源：

TETRAHEDRON | 1979年 / 35卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(01)99493-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of some 7-substituted-3-azabicyclo[3.3.1]nonanes is described. Routes followed were the debenzoylation of the 7-benzoyl derivative 7 and the decarboxylation of the 7-carboxy compounds 21 and 27. The so-obtained 7-oxo-N-tosyl-3-azabicyclo[3.3.1]nonanes 8and 11 show an extremely low reactivity towards a series of nucleophilic reagents. From analysis of the 1H NMR spectral data of a series of derivatives, the twin-chain conformation for the 7-exo compounds and the chair-boat conformation for the 7-endo compounds is indicated. © 1979.

引用

页码：267 / 272

页数：6

共 12 条

[1] BOK TR, 1977, TETRAHEDRON, V33, P787
[2] BOK TR, 1978, TETRAHEDRON LETT, P657
[3] BOK TR, UNPUBLISHED
[4] NATURE OF SIGMA-COUPLED TRANSITIONS - THROUGH-BOND INTERACTIONS IN 1-AZA-ADAMANTANE DERIVATIVES
DEKKERS, AWJ
VERHOEVE.JW
SPECKAMP, WN
[J]. TETRAHEDRON, 1973, 29 (12) : 1691 - 1696
[5] LOVEN R, 1973, THESIS U AMSTERDAM
[6] MOMOSE T, 1974, TETRAHEDRON LETT, P3697
[7] SYNTHESIS OF SUBSTITUTED 3-AZA-BICYCLO[3.3.1]NONANES
SPECKAMP, WN
DIJKINK, J
DEKKERS, AWJ
HUISMAN, HO
[J]. TETRAHEDRON, 1971, 27 (14) : 3143 - &
[8] SPECKAMP WN, 1970, CHEM COMMUN, P197
[9] STETTER H, 1974, LIEBIGS ANN CHEM, P1322
[10] TRAAS PC, 1976, TETRAHEDRON LETT, P2287

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