SYNTHESIS AND MASS-SPECTRA OF SUGAR THIOIMIDAZOLE DERIVATIVES

The reaction of 1-halogenophenylglucofuranoimidazolidine-2-thiones (1, 2) with benzyl chloride gives bicyclic S-benzylthioimidazolines (3, 4 ) or tetrahydroxybutyl S-benzylthioimidazoles (7, 8) depending on the presence or absence of sodium hydrogencarbonate. In the latter case a partial desulphuration takes place. The electron impact mass spectra o f compounds 1-4, 7, 8, and of the acetyl derivatives 5, 6, 9, and 10 a re examined. The primary fragmentations and two fragmentation pathways were observed, the importance of which depends on the cyclic characte r of the molecule and of the nature of the substituent (OH or OAc).