Generation and synthetic applications of 2-lithio-1,3-dithianes

A novel synthesis of 2,4,6-trithiaheptane and its conversion into 2,6-bis(methylthio)thiane. Spectral properties of some thiaalkanes

“…We have found that l c could be generated readily under standard conditions (3) and that it reacted efficiently with standard electrophiles, such as iodomethane to give 3-methyl-2,4,6-trithiaheptane, I 3a, or with 1-bromobutane to yield the n-butyl derivative, 36. Quenching l c with deuteroacetic acid gave 3c, but of more interest was the reaction of l c with 1-bromo-3-chloropropane which gave 3d, a compound that had potential for ring closure by a two-step reaction.…”

Acyl anion synthons: benzotriazole stabilized compared to classical

“…1,3-Dithianes have been successfully used in reactions with (i) alkyl halides, sulfonates and triflates; [23][24][25][26][27][28] (ii) oxiranes 23,[29][30][31] and three-to six-membered cyclic ethers; 29 (iii) carbonyl compounds; 23,32,33 (iv) acid halides 34,35 and chloroformates; 29,36,37 (v) imines; 23 and (vi) electron deficient olefins [38][39][40] (Scheme 6). …”

A Novel Synthesis of Branched High-molecular-weight (C40+) Long-chain Alkanes

“…Lithiation of 1,3-dithiane (3) was performed according to the literature procedure, 42) and THF was freshly distilled from sodium W benzophenone. All reactions were carried out under a nitrogen at- General Procedure for the Preparation of a,vBis(dithianyl)alkanes 1a-c (Table 1).…”