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Methyl Rearrangement of Methoxy-Triazines in the Solid- and Liquid-State

✍ Scribed by Eidit Handelsman-Benory; Mark Botoshansky; Mark Greenberg; Vitaly Shteiman; Menahem Kaftory

Book ID: 104202840
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 221 KB
Volume: 56
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(00)00510-x

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✦ Synopsis

AbstractÐ2,4,6-Trimethoxy-1,3,5-triazine 11, and 6-methoxy-3,5-dimethyl-tetrahydrotriazine-2,4-dione 13 undergo intermolecular O3N methyl rearrangement in the liquid-state to 1,3,5-trimethyl 2,4,6-trioxohexahydro-s-triazine 14. 4,6-Dimethoxy-3-methyl-dihydro-triazine-2-one 12 was found to exhibit a different thermal behavior, and the methyl rearrangement takes place in the solid-state. The thermal behavior of each was investigated by calorimetry and high-temperature X-ray diffraction. It was found that 11 undergo phase transition to 11 H , and the methyl rearrangement takes place in the melt. The solid-state methyl rearrangement of 12 is topochemically controlled. Two courses of methyl migration in the solid-state of 12 are proposed. A quantitative analysis of samples of 12 heated to different temperatures proves the existence of the two courses. A computer simulation was used to rationalize the reaction routes in 12 and 13.

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