129110-70-9

Upstream product

• 1450-31-3 Thiobenzophenon 
• 22186-76-1 3,4-Diphenyl-Δ¹-1,2,3-triazolin-5,5-dicarbonsaeure-dimethylester 
• 34671-09-5 dimethyl 1,3-diphenylaziridine-2,2-dicarboxylate 

Relevant academic research and scientific papers

1,3-Thiazolidine-dicarboxylates from thioketones and thermally generated azomethine ylides

The reaction of 9H-fluorene-9-thione (1) with the cis- and trans-isomers of dimethyl 1-(4-methoxyphenyl)- Saziridine-2,3-dicarboxylate (cis- and trans-2, resp.) in xylene at 110° yielded exclusively the spirocyclic cycloadduct with trans- and cis-configurations, respectively (trans- and cis-3; resp.; Scheme 1). Analogously, less-reactive thioketones, e.g., thiobenzophenone (5), and cis-2 reacted stereoselectively to give the corresponding trans-1,3-thiazolidine-2,4-dicarboxylate (e.g., trans-8; Scheme 2). On the other hand, the reaction of 5 and trans-2 proceeded in a nonstereoselective course to provide a mixture of trans- and cis-substituted cycloadducts. This result can be explained by an isomerization of the intermediate azomethine ylide. Dimethyl 1,3-thiazolidine-2,2-dicarboxylates 14 and 15 were formed in the thermal reaction of dimethyl aziridine-2,2-dicarboxylate 11 with aromatic thioketones (Scheme 3). On treatment of 14 and 15 with Raney-Ni in refluxing EtOH, a desulfurization and ring-contraction led to the formation of azetidine-2,2-dicarboxylates 17 and 18, respectively (Scheme 4).

Dimethyl 3,4,5,5-tetraphenyl-1,3-thiazolidine-2,2-dicarboxylate and 3,3-dichloro-2,2,4,4,3′-pentamethyl-r-2′,t-4′- diphenylcyclobutane-1-spiro-5′-1,3-thiazolidine

The first of the title compounds, C31H27NO 4S, (V), crystallizes in the monoclinic space group P21c with two independent molecules in the asymmetric unit, while the second, C 23H27Cl2NS, (IX), crystallizes in the orthorhombic space group Pbca with one molecule in the asymmetric unit. In both crystal structures, the 1,3-thiazolidine ring adopts a half-chair conformation. The crystal structures are stabilized by weak C-H· · ·O and C-H· · ·Cl hydrogen bonds in (V) and (IX), respectively.

1,3-DIPOLAR CYCLOADDITIONS OF SOME AZOMETHINE YLIDES TO THIOKETONES

Reactions of the azomethine ylides generated from cis-1-substituted-2,3-diphenylaziridines 1a-b or from 1,2,3-triazoline 5 with thiobenzophenone, adamantanethione and 2,2,4,4-tetramethyl-3-thioxocyclobutanone are described.