134897-08-8Relevant articles and documents
Methyl 2-Methyldithiocarbazate in Heterocyclic Synthesis: Preparation of 2,5-Disubstituted 1,3,4-Thiadiazoles, Bis(1,3,4-Thiadiazolium) Salts and Macrocycles containing 1,3,4-Thiadiazole Subunits. X-Ray Crystal Structure of 2,2'-Bis<4,5-dihydro-5-(2-hydroxyethylimino)-4-methyl-1,3,4-t...
Molina, Pedro,Espinosa, Arturo,Tarraga, Alberto,Cano, Felix Hernandez,Foces-Foces, Ma. Concepcion
, p. 1159 - 1166 (2007/10/02)
Reaction of the iminophosphorane 2, derived from methyl 2-methyldithiocarbazate and triphenylphosphine, with carbon disulphide gives the mesoionic compound 3, which reacts with α,ω-dihalogeno compounds to give bis-(1,3,4-thiadiazolines) 7-9.However, reaction with ethylenediamine or 1,4-tetramethylenediamine leads to macrocycles 11 and 12.Methyl 2-methyldithiocarbazate, by sequential treatment with dicarboxylic acid chlorides and perchloric acid, leads to the bis-(1,3,4-thiadiazolium) salts 19-21, which undergo nucleophilic displacement of the methylthio group, uponreaction with β-substituted ethylamines, to give products 22-28.The crystal structure of compound 22 has been determined by X-ray crystallography.The crystal should be described in a P1 cell, with parameters a=11.2862(17), b=7.7409(8), c=4.2676(2) A, α=93.441(5), β=91.703(6) and γ=108.780(12) deg.The molecule presents an internal crystallographic inversion centre, and the terminal OH groups are disordered between two tetrahedral positions of the bonded carbon atom.
