Aziridines. XVIII. The Pyrolytic and Iodide Ion Catalyzed Rearrangements of the cis- and trans-l3-p-Nitrobenzoyl-13-azabicyclo [10.1.0] tridecanes

Ilene J. Burnstein, Paul E. Fanta, Bernard S. Green

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Abstract

Pyrolysis of trans-13-p-nitrobenzoyl-13-azabicyclo[10.1.0]tridecane (3) in toluene at 110° gave a mixture of trans-N-(2-oyolododeoenyl)-p-nitrobenzamide (6) and cis-N-(2-oyolododecenyl)-p-nitrobenzamide (5) in a ratio of 2:1. Pyrolysis of cis-13-p-nitrobenzoyl-13-azabieyclo[10.1.0]tridecane (4) in xylene at 140° gave a mixture of 6 and trans-2-p-nitrophenylcyclododecano[4,5-d]oxazoline (7) in a ratio of 7:1. Reaction of 4 with sodium iodide in acetone gave cis-2-p-nitrophenylcyclododecano[4,5-d]oxazoline (12). The formation of these products was rationalized in terms of the probable conformations of 3 and 4 and their respective transition states as deduced from the reported conformations of the corresponding aziridinium methiodides found by X-ray studies.

Original languageEnglish
Pages (from-to)4084-4087
Number of pages4
JournalJournal of Organic Chemistry
Volume35
Issue number12
DOIs
StatePublished - 1 Dec 1970
Externally publishedYes

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