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Reactions of triazolinediones with cis-alkenes. A highly regioselective ene reaction

✍ Scribed by Yiannis Elemes; Manolis Stratakis; Michael Orfanopoulos

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
223 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

The ene reaction of tiazolinedione with unsymmetrical cis-alkenes is regiospecific and shows a preferential abstraction of the allylic hydrogens on the larger alkyl group of the double bond.

Triazolinedione

(PTAD) undergoes the same type of reactions as singlet oxygen (102). It reacts rapidly

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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 doublebo