158727-08-3Relevant articles and documents
1,3-bis(phenylmercapto)propane and 1-chloro-3-(phenylmercapto)propane: Useful precursors for 1,3-dilithiopropane synthons in the preparation of 1,5- diols
Foubelo, Francisco,Yus, Miguel
, p. 5047 - 5051 (2007/10/03)
Treatment of 1,3-bis(phenylmercapto)propane (1) with an excess of lithium and a catalytic amount of DTBB (3.5 mol%) at -78°C followed by reaction with a carbonyl comPOund [BuCHO, PhCHO, (PhCH2)2CO, Et2CO, (CH2)7CO, [(CH2)7CO])-menthone, Ph2CO] leads, after hydrolysis with water, to symmetrically substituted 1,5-diols (2). Starting from 1-chloro-3- (phenylmercapto)propane (3) and by successive treatment with: (a) lithium- naphthalene at -78°C; (b) a carbonyl compound {Me2CO, (CH2)5CO, (CH2)7CO, (-)-menthone, [CH3(CH2)4]2CO] at the same temperature; (c) lithium powder at -50°C; and (d) a second carbonyl compound ['BuCHO, PhCHO] at the same temperature and final hydrolysis with water yields unsymmetrically substituted 1,5-diols (4). (C) 2000 Elsevier Science Ltd.