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An Interplay in the Regioselectivity Induced by Non Bonding Interactions, in the ene Reactions of Singlet Oxygen and Triazolinediones with Tetrasubstituted Alkenes

✍ Scribed by Yiannis Elemes; Manolis Stratakis; Michael Orfanopoulos

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 530 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)01471-8

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✦ Synopsis

The ene reactions of N-phenyl-l.2,4-triazoline-3S-dione (p'f'AD)and singlet oxygen (102) with tetrrrsubstihrted sfkenes,follow regioselectivitytrendsgovernedmairrtyby 1,3-non bondedinteractions(typeI) for the case of ITAD, and mainfyby the steric hindrancecausedduringthe formationof the new doublebond (type II) for the case of 102. The resnftsare explainedin termsof a "late"productformingtransition stateof hydrogen abstraction for triazotinedionea and an "early"transition statefortbesnsfogous singlet oxygenreaction.

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