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Synthetic Applications of Heteroaromatic Betaines with Six‐Membered Rings
Author(s) -
Dennis Nicholas,
Katritzky Alan R.,
Takeuchi Yoshito
Publication year - 1976
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197600011
Subject(s) - quantum chemical , rationalization (economics) , chemistry , computational chemistry , stereochemistry , molecule , organic chemistry , philosophy , epistemology
The cycloadditions of 3‐hydroxy‐1‐methylpyridinium betaines with electron‐deficient olefins have been extended to a variety of 1‐substituents in place of methyl. Application of resonance theory and later of quantum chemical methods led to rationalization of preceding results and prediction of new reactions. Thermal additions of 2π‐ and 6π‐electron addends at the 2,6‐positions and of 4π‐electron addends at the 2,4‐positions are described. The cycloadducts are highly interesting potential synthetic building blocks.