Conformational studies of N3-substituted [1,3,4]-oxadiazinan-2-ones

被引：24

作者：

Casper, DM ^{[1
]}

Blackburn, JR ^{[1
]}

Maroules, CD ^{[1
]}

Brady, T ^{[1
]}

Esken, JM ^{[1
]}

Ferrence, GM ^{[1
]}

Standard, JM ^{[1
]}

Hitchcock, SR ^{[1
]}

机构：

[1] Illinois State Univ, Dept Chem, Normal, IL 61790 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 25期

关键词：

D O I：

10.1021/jo020322g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pseudoephedrine-based [1,3,4]-oxadiazinan-2-ones acylated at the N-3-position with either acetyl (2a), propionyl (2b), or phenylacetyl (2c) substituents are known to undergo conformational changes that are observable by C-13 NMR spectroscopy. The conformational properties of new [1,3,4]oxadiazinan-2-one derivatives 2d-k are examined by X-ray crystallography and variable-temperature C-13 NMR spectroscopy and further evaluated by semiempirical AM1 calculations. The collected data reveal that the conformational changes of the overall ring system are dependent upon the stereoelectronic factors of the N-3-substituent.

引用

页码：8871 / 8876

页数：6

共 17 条

[1]

de Parrodi CA, 2001, TETRAHEDRON-ASYMMETR, V12, P69

[2]

DORMAN L, 1967, J ORG CHEM, V32, P5

[3] CONFORMATIONAL-ANALYSIS OF SATURATED HETEROCYCLES .72. TETRAHYDRO-1,3,4-OXADIAZINES [J].