DIAZOCINE CHEMISTRY .4. RING CONTRACTIONS TO DIAZEPINES AND PIPERIDINES

被引：6

作者：

PAUDLER, WW

ZEILER, AG

GAPSKI, GR

机构：

[1] Department of Chemistry, Clippinger Laboratories, Ohio University, Athens, Ohio

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 04期

关键词：

D O I：

10.1021/jo01256a051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of cis- and trans-diazocine derivatives 1 and 2 with thionyl chloride afforded cis- and trans-diazepines 3 and 5, respectively, trans compound 2 also yielded trans-piperazine 4. Similar ring-contracted diazepines were obtained from cis- and trans-tetratosyl derivatives 7 and 8. Free aminediols 11 and 12 were prepared by hydrolysis of N,N′-ditosyl compounds 1 and 2. cis-Diol 13 rearranges, when passed over hot alumina, to 2-methyl- (14), 2,5-dimethyl- (15), 2,6-dimethyl- (16), and 2,3,5-trimethylpyrazine (17). The mode of formation of these compounds is described in terms of the involvement of intermediate aziridinium ions. © 1969, American Chemical Society. All rights reserved.

引用

页码：1001 / &

共 8 条

[1] REACTION KINETICS OF ALIPHATIC TERTIARY BETA-CHLOROETHYLAMINES IN DILUTE AQUEOUS SOLUTION .3. REACTIONS OF THE ETHYLENIMONIUM ION WITH CERTAIN ANIONS [J].