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Cycloaddition of Bifunctional Nitrones to Monosubstituted Alkenes, I
Author(s) -
Moskal Janusz,
Milart Piotr
Publication year - 1985
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19851181014
Subject(s) - nitrone , chemistry , regioselectivity , cycloaddition , bifunctional , reactivity (psychology) , bicyclic molecule , 1,3 dipolar cycloaddition , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Cycloaddition of bifunctional nitrones 1 containing a nitrone function as part of the 1,4‐diazabutadiene system to electron‐rich monosubstituted alkenes has been investigated. The nitrone group manifested predominant 1,3‐dipolar reactivity compared with that of the 1,3‐heterodiene system leading to isoxazolidine derivatives 2 and 3 . An atypical assistance of the 1,4‐diazabutadiene system was demonstrated by a reverse regioselectivity of cycloadditions to allyl alcohol yielding bicyclic heterocycles 2 via 3,4‐disubstituted isoxazolidines. Cycloadditions with allyl halides gave 3,5‐disubstituted isoxazolidines 3 showing common regioselectivity for the nitrone function. The mechanism and configuration of the products are discussed.