77566-35-9Relevant articles and documents
Preparations et essais d'heterocyclisation radicalaire de nitrites et N-chloroamines acetyleniques
Dupuy, Claude,Surzur, Jean-Marie
, p. 374 - 380 (2007/10/02)
Nitrites RCC(CH2)nONO and N-chloroamines RCC(CH2)nN(Et)Cl (n = 3,4; R = H,Ph,Me) have been treated so as to form the corresponding heteroatomic radicals.In the case of nitrites, a product resulting from intramolecular addition of the alkoxy radical to the triple bond could be isolated only for n = 3.This product, which was obtained with a very poor yield, is the γ-butyrolactone resulting from decomposition of a primary product not isolated.When n = 4 and R = H, an isoxazole which could derive from an initial step consisting of the intramolecular abstraction of a propargylic hydrogen was formed.With acetylenic N-chloramines, we could not identify any product resulting from intramolecular addition of an aminyl radical to the triple bond.These rather poor synthetic results are compared to the much better ones obtained by intramolecular addition of the thiyl radical to the acetylenic system, and the origin of this difference in behaviour is discussed.