ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
1-Aza-bicyclo[2.2.0]hexane (1) is formed in a unimolecular reaction from 2-(2-bromoethyl)-azetidine (13) in aqueous or alcoholic medium. Thermal instability and high reactivity have, however, so far precluded its isolation. Hydrochloric acid, aqueous sodium hydroxide and ethanolic sodium ethoxide convert the bicyclic amine 1 into 4-chloro-, 4-hydroxy- and 4-ethoxy-piperidine, (14), (15) and (16), respectively. Upon heating in solution to ca. 80° it undergoes fragmentation to N-methylene-3-butenyl-amine (17). This unusual reactivity is ascribed to strain and to concomitant weakening of the N-C4 bond in the bicyclic amine 1.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19640470808
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