Diallyl thioether

Synonyms cas 592-88-1 allyl monosulftoe diallyl sulhde diallyl thioether oil garlic tidoallyl... 

The first proposal of intramolecular addition of 5-hexenyl radicals was independently reported in 1957 by Marvel and by Butler. They polymerized 1,6-dienes and, finding that the products were devoid of unsaturation, assumed that the initially produced radicals had cyclized their work will be discussed in a later section. Also to be discussed is the pioneering work of Friedlander who, in 1958, reported the cyclization of diallyl ethers and diallyl thioethers under free radical conditions. 

Triazines are generally more reactive in [2 + 4] cycloaddition in comparison with 1,2,3-tria-zines. The wide variety of dienophiles can be employed enamines, enaminones, vinyl silyl ethers, vinyl thioethers, cyclic ketene jV,O-acetals, /V-phenylmaleimide, 6-dimethylaminopentafulvene, 2-alkylidene-imidazolidines (cychc ketene aminals), cyclic vinyl ethers, arynes, benzocyclopropene, acetylenes, and alkenes like ethylene, (Z)-but-2-ene, cyclopentene, cyclooctene and bicyclo[2.2.1]hept-2-ene, hexa-1,5-diene, cycloocta-1,5-diene, diallyl ether, cyclododeca-l,5,9-triene,... 

Dimethyl-l,4-thiaselenin (59) is synthesized by the dehydrobromination of 3,5-di(bromo-methyl)-l,4-thiaselenane (58) by sodium methoxide (Equation (13)). This method can also be applied to the synthesis of other 3,5-dialkyl-l,4-dichalcogenines, which are obtained from diallyl ethers or thioethers (see Scheme 18) <77KGS58>. 

Wargovich MJ, Woods C, Eng VW, Stephens LC, Gray K. Ghemoprevention of N-nitrosomethylbenzylamine-indnced esophageal cancer in rats by the naturallyoccurring thioether, diallyl sulfide. Cancer Res 1988 48 6872-6875. 

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