Rigid core vinamidinium salts and their N,N′-rotamers

被引：6

作者：

Ostercamp, DL ^{[1
]}

Dinh, Y ^{[1
]}

Graff, D ^{[1
]}

Wiles, S ^{[1
]}

机构：

[1] Concordia Coll, Dept Chem, Moorhead, MN 56562 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 08期

关键词：

D O I：

10.1021/jo020654l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The power of proton magnetic resonance spectroscopy to unravel stereochemical details is amply demonstrated. O-Methylation of 3-methylamino-5,5-dimethyl-2-cylohexen-l-one (1a) produces stable diastereomers, (Z)- and (E)-N-(3-methoxy-5,5-dimethyl-2-cyclohexen-1-ylidine)-N-methylaminium iodide (2a). As predicted by computation and confirmed by spectroscopy, the (Z)-vinylogous imidate salt predominates. Reaction of 2a with primary and secondary amines furnished a number of vinamidinium salts, including N-(3-methylamino-5,5-dimethyl-2-cyclohexen-1-ylidene)-N-methylaminium iodide (3a). Two rotamers of 3a were identified and characterized. A substantial number of additional compounds 2 and 3 are included in the study.

引用

页码：3099 / 3105

页数：7

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