Homopolycondensation of 1-halogenopropane-2-thiones

Abstract

Homopo}ycondensation of l-halogenopropane-2-thiones was studied; the polymers obtained were strttcturally characterized by ESR. UV, and IR spectroscopy, elemental analysis, and electrochemical methods. Their molecular masses, dark conductivities, and photoconductivities were determined The capability fi~r film formation on variotLs substrates was investigated. These polymers were found to be new organic metals (Hal = I). semiconductors (Hal = CI and Br). and photoconductors (Hal = CI. Br)

Reactions of Aldehydes and Ketones and their Derivatives

“…Trimethylsilyl triflate catalyses diastereoselective ring-opening reactions of semicyclic N ,O-acetals (4) with nucleophiles such as silyl enol ethers. 2 ᭺ de (1) ( Acetal (5), with a tethered acyloin, undergoes an intramolecular geminal acylation, catalysed by boron trifluoride etherate, to give 1,3-diketone (6). 3 The mechanism necessarily differs from the intermolecular version.…”

“…A new thioacetal, 1-chloro-2-mercapto-propan-2-ol (10), has been isolated from the treatment of 1-chloro-2-propanethione (9) with hydrochloric acid; in the presence of water it cyclizes to 2,4,6-tris(chloromethyl)-2,4,6-trimethyl-1,3,5-trithiane (11). 6 A stereoelectronic correlation of the relative rates of hydrolysis of ketone-derived acetals with their proton affinities considers both cyclic and acyclic cases. 7 Terminal isopropylidene acetals have been chemoselectively hydrolysed to the corresponding 1,2-diols using Yb(OTf) 3 •H 2 O.…”

10.1007/s11178-008-1003-1

“…By reactions of α-halo thiones and α-halo dithiols with various nucleophilic and electrophilic reagents we succeeded in purposefully obtaining a variety of heterocyclic systems, such as thiiranes [3], 1,4-dithianes [4], 1,3,5-trithianes [5], 2,3,5,6-tetrathianes [6], 2-sulfanyl-2-methyltetrahydro [1,4]thiazinoquinolinium halides [7], dithiiranes [8], 1,4-dithiines [9], and 1,3,4-thiadiazines [10], including those possessing biological activity. The ability of 1-halopropane-2-thiones to readily undergo homopolycondensation at 20°C to give polymeric products having paramagnetic, conducting, and photoconducting properties [11] underlies their possible application in the development of materials and coatings of practical importance. 1-Chloropropane-2,2-dithiol and 2-sulfanyl-2-methyltetrahydro [1,4]thiazinoquinolinium halides can be used as components for the design of pharmacological agents for neutralization of very stable and highly toxic alkylmercury cations [12].…”