13597-15-4Relevant academic research and scientific papers
Synthesis of six- and seven-membered heterocycles by reaction of 1-(2-chloroethylthio)-1-alkynes and 1-(3-chloropropylthio)-1-alkynes with alkali metal sulfide, selenide and telluride
Sukhai, R. S.,Jong, R. de,Verkruijsse, H. D.,Brandsma, L.
, p. 368 - 372 (2007/10/02)
Reaction of RCC-S-CH2CH2Cl (1, R=alkyl) compounds with dilithium disulfide (Li2S2) in ethanol gives 3-alkyl-5,6-dihydro-1,4-dithiins (2, n=2, X=S).With the alkali monosulfide, M2S, dehydrochlorination to (vinylthio)alkynes RCC-S-CH=CH2 (3) predominates.Interaction between 1, n=2, and M2Se or M2Te (M=Li or Na) in liquid ammonia gives rise to dehydrochlorination as well as to attack on chlorine with intermediate formation of alkynethiolates RCC-S- (4); if this reaction is carried out in ammonia-free ethanol, the desired 5,6-dihydro-1,4-thiaselenins and -thiatellurins (2, n=2, X=Se or Te) are, in some cases, obtained.The chloro sulfides RCC-S-(CH2)3Cl (1, R=alkyl or phenyl) with alkali metal sulfide, selenide and telluride yield respectively 3-alkyl- or 3-aryl-6,7-dihydro-5H-1,4-dithiepins, the corresponding 6,7-dihydro-5H-1,4-thiaselenepins and 6,7-dihydro-5H-thiatellurepins (2, n=3).When R in the starting compounds 2 is a Me3Si group, the unsubstituted compounds 2 (n=3, R=H) are formed.
