Synthesis of (2-alkylthiothiazolin-5-yl)methyl dodecanoates via tandem radical reaction
A series of (2-alkylthiothiazolin-5-yl)methyl dodecanoates was synthesized from various alkyl N-allylcarbamodithioates and dilauroyl peroxide via a tandem radical hydrogen-abstraction-cyclization-substitution/combination reaction with a 5-exo-trig radical cyclization as a key step. The current route is the first, convenient, and efficient synthesis of (2-alkylthiothiazolin-5-yl)methanol derivatives. The Royal Society of Chemistry.
Kakaei, Saeed,Xu, Jiaxi
p. 5481 - 5490
(2013/08/28)
Radical Nature of Pathways to Alkene and Ester from Thermal Decomposition of Primary Alkyl Diacyl Peroxide
Thermal decomposition of a primary alkyl diacyl peroxide 2 is investigated.Dependence of product yields on temperature, viscosity, and solvent polarity is examined in a variety of media.The excess of the alkene disproportionation product 4 and the presence of ester 3 and acid 5 is argued to demonstrate the existence of a discrete acyloxy-alkyl geminate radical pair.Stereoselective deuterium labeling of 2 and subsequent 1H-NMR analysis of the resulting isotopomers of 4 confirm the radical nature of detected decomposition products.
Ryzhkov, Lev R.
p. 2801 - 2808
(2007/10/03)
ETUDE DES REACTIONS DE SUBSTITUTION HOMOLITIQUE SUR LE NOYAU PYRIDINIQUE; INFLUENCE DE L'ACIDITE DU MILIEU
Homolytic substitution by the 1-n-undecyl radical at positions 2 and 4 of the pyridine nucleus results from thermal decomposition of dodecanoyl peroxide in acetic acid.Rate dependence on pH shows that pyridine protonation increases the rate of addition of the alkyl radical to the pyridine ring but decreases the rate of the reaction of the intermediate radical with the peroxide.Results are interpreted in terms of orbital interaction theory.
Sebedio, J. L.,Sorba, J.,Fossey, J.,Lefort, D.
p. 2829 - 2842
(2007/10/02)
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