13865-06-0

Upstream product

• 35364-99-9 α-chlorobenzyl methyl ether 
• 124-41-4 sodium methylate 
• 82834-06-8 Methoxy-methylsulfanyl-phenyl-acetaldehyde 
• 14755-55-6 α-benzoyl-α-(methylthio)methyl chloride 
• 117139-83-0 O-ethyl S-(α-methoxy-benzyl)dithiocarbonate 
• 74-88-4 methyl iodide 
• 5873-86-9 methyl thiobenzoate 

Relevant academic research and scientific papers

α-Thio-substituted Ketones as Precursors of Olefins via Oxathiolanes: α-Methoxybenzyl as Protecting Group

A number of routes to 2-(α-methoxybenzylthio) ketones (3) have been explored with a view to their use as precursors of substituted 2-phenyl-1,3-oxathiolanes.The most successful preparation of compounds (3; R1=Ph) and (3; R1 = Me) involved the in situ generation of the appropriate α-mercapto ketone (10) from an α-oxo dithiocarbonate and alkylation with α-methoxybenzyl chloride.Lithium aluminium hydride reduction of ketone (3; R1 = Ph) followed by cyclisation to 2,5-diphenyl-1,3-oxathiolane (11) provided a prototype for the approach outlined in Scheme 1 but Grignard and organolithium reagents did not react clearly with ketone (3) to give a general route to protected β-mercapto alcohols.Treatment of the β-oxo dithiocarbamate (13; R1 = Ph) with base and alkyl halide under phase-transfer catalysis conditions gave the enol derivative (14) by sulphur to oxygen migration followed by alkylation at sulphur.

MIGRATION DU CARBONYLE : OBTENTION D'HOMOLOGUES DU GLYOXAL A FONCTION CETONIQUE PROTEGEE

Substituted glyoxals with protected ketogroup 3 were obtained by reaction of α-chloro-α-(aryl- or alkyl-thio)ketones 1 with sodium methylate in methanol.

Electroreduction of Organic Compounds, 2. - Preperation of Dithioacetals by Electroreductive Alkylation of Alkyl Dithiocarboxylates

Alkyl Dithiobenzoates 1 and O-methyl thiobenzoate (7) yield the benzaldehyde dithioacetals 2 or monothioacetals 8, respectively, by electroreduction in the presence of alkyl halides.The S-acylal 3b is formed from ethyl dithiobenzoate 1b in the presence of acetic anhydride. - The dithioacetals 5 and the ketene dithioacetals 6 are obtained by co-electroreduction of methyl dithiopropionate (4) with alkyl halides. - Conclusions about the reaction mechanism are drawn from voltammetric measurements.