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1,3‐Dipolar addition of formonitrile oxide, and hydroxyiminoacetonitrile oxide to some olefins. The synthesis of isoxazolidino[2,3‐ b ]‐Δ 3 ‐l,2,5‐oxadiazolines
Author(s) -
Fajkos J.,
Edwards J. A.
Publication year - 1974
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570110113
Subject(s) - chemistry , yield (engineering) , oxide , base (topology) , substrate (aquarium) , medicinal chemistry , organic chemistry , mathematical analysis , materials science , oceanography , mathematics , metallurgy , geology
The 1,3‐dipolar addition of formonitrile oxide and hydroxyiminoacetonitrile oxide to a variety of olefins is described. The 3‐anti‐aldoximino‐Δ 2 ‐isoxazolines, resulting from the addition of the dimerie hydroxyiminoacetonitrile oxide to the olefinie substrate, undergo base‐catalyzed cyclization to yield novel isoxazolidino[2,3‐ b ]‐Δ 3 ‐l,2,5‐oxadiazolines. The latter products are rearranged to α‐oximino‐γ‐lactones after additional treatment with base.