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STUDIES ON ORGANOPHOSPHORUS COMPOUNDS-XL. REACTIONS OF KETONES WITH 2,4-BIS(4-METHOXYPHENYL)-1,3,2,4-DITHIADIPHOSPHETANE 2,4-DISULFIDE
Scheibye, S.,Shabana, R.,Lawesson, S.-O.,Romming, C.
, p. 993 - 1002 (2007/10/02)
Cyclohexanone and cyclopentanone react with (2,4-bis-4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson Reagent (LR)) at 80 deg C with formation of new spiro-1,3,5,2-trithiaphosphorines 1 and 2, respectively. 2-Methyl and 2-phenylcyclohexanone also react with LR at 80 deg C producing the enethiols 3 and 4, which on storage are transformed into the sulfides 5 and 6.Unsaturated cyclohexanones 7-9 are transformed into the corresponding thioketones 10-12 after reactions with LR at 60 deg C for a few hours. 2-Hydroxyketones react with LR with formation of 1,3,2-oxathiaphospholes and similarly a 2-aminoketone gave a 1,3,2-thiazaphosphole.Aromatic ketones, reacted with LR to give corresponding thioketones.Thiofluorenone dimerized to form the cyclic disulfide 31, as proved by X-ray analyses.
