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Regioselectivity of ring closure of the 2-azonia-2,2,5-trimethyl-5-hexenyl radical

✍ Scribed by Ernest W Della; Paul A Smith

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 71 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01987-0

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✦ Synopsis

The 2-azonia-2,2,5-trimethyl-5-hexenyl radical 9, derived from treatment of 1-iodo-2,2,5-trimethyl-2-azonia-5-hexenyl iodide 12 with tributyltin hydride, is found to give an 8:3:1 mixture of the isomeric 5-exo, 6-endo and acyclic ammonium salts. A rationale for the observed regioselectivity is proposed, and a comparison is made with the behaviour of the corresponding all-carbon radical.

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