195154-38-2

Upstream product

• 1123-34-8 1-allyl-1-cyclohexanol 
• 108-98-5 thiophenol 
• 502-42-1 cycloheptanone 
• 28118-53-8 1,3-bis(phenylthio)propane 
• 108-94-1 cyclohexanone 
• 4911-65-3 3-chloropropyl phenyl sulfide 

Downstream Products

• 101083-14-1 1-[3-(1-hydroxycyclohexyl)propyl]cyclohexanol 
• 4481-78-1 1-oxa-spiro[5.5]undecan-2-one 

Relevant academic research and scientific papers

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

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.

Synthesis and Applications of Tetrahydrofuran-Stable Substituted (3-Lithioxyalkyl)- and (4-Lithioxyalkyl)lithiums, Modified with Magnesium 2-Ethoxyethoxide

Substituted hydroxyalkyl phenyl sulfides 3 have been synthesized from the corresponding allylic or homoallylic alcohols 2. Regiospecific cleavage of the C - SPh bond of the sulfides 3 by lithium dispersion in tetrahydrofuran (THF) led to the synthesis of substituted (3-lithioxyalkyl)- and (4-lithioxyalkyl)lithiums 4, most of which share the ω carbon with a carbocyclic ring. The organolithiums were modified with magnesium 2-ethoxyethoxide in order to suppress their reactivity toward THF cleavage, thus offering the advantage of preparing storable ethereal solutions of certain types of (lithioxyalkyl)lithiums. This strategy appears to be of rather broad scope. The functionalized organolithiums prepared in this way react normally with electrophilic reagents with yields in the range 35-55%. Thus, carboxylations of 4 yielded lactones 5, some of which are natural products, while reactions of 4 with benzophenone and cyclic ketones yielded 1,4- and 1,5-diols 6 and 7, respectively.