105494-85-7

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 6947-57-5 cyclohexyl phenyl sulfone 
• 7570-92-5 cyclohexyl phenyl sulphide 
• 108-85-0 1-bromocyclohexane 
• 108-98-5 thiophenol 

Downstream Products

• 6947-57-5 cyclohexyl phenyl sulfone 
• 137345-43-8 1-cyclohexyloxomethyl-1-(phenylsulfonyl)cyclohexane 
• 130837-22-8 1-cyclohexyloxomethyl-1-(ortho-trimethylsilylphenylsulfonyl)cyclohexane 
• 137345-47-2 1-(ortho-cyclohexylhydroxymethyl)phenylsulfonyl-1-trimethylsilylcyclohexane 
• 137345-46-1 1-cyclohexylhydroxymethyl-1-(ortho-trimethylsilylphenylsulfonyl)cyclohexane 
• 137345-42-7 1-cyclohexylhydroxymethyl-1-(phenylsulfonyl)cyclohexane 
• 137345-41-6 1-phenyloxomethyl-1-(phenylsulfonyl)cyclohexane 

Relevant academic research and scientific papers

Scope and limitations in the use of α-silyl and α-stannyl sulfones as latent α-sulfonyl anions

Three methods for the regeneration of α-sulfonyl anions from α-silyl sulfones and α-stannyl sulfones are investigated. These methods include: (1) treatment of α-silyl sulfones with electrophiles (aldehydes and acid halides) in the presence of fluoride ion; (2) reaction of α-silyl sulfones with n-butyllithium which produces an α-silyl anion via a migration of the -SiMe3 group from the α-position to the ortho-position of the phenyl sulfones; and (3) direct transmetalation of α-stannyl sulfone by treatment with n-butyllithium. The addition of cerium [III] chloride is shown to substantially decrease enolization problems associated with addition of α-sulfonyl anions to carbonyl compounds bearing enolizable protons.

The Synthesis of Ketones via α-Silyl Sulphides

α-Phenylthiosilanes (2) have been prepared by alkylation of the anion (4) derived from the 1-phenylthio-1-trimethylsilylalkane (1).These anions (4) have benn prepared by a variety of methods including, direct deprotonation of (1), displacement of a phenylthio group by lithium naphthalenide addition of an alkyl-lithium to 1-phenylthio-1-trimethylsilylethene (7), and transmetallation of a tributylstannyl moiety.The formation of an alkyl-lithium by reaction of lithium naphthalenide with a phenyl sulphide provided an additional route to (2) from bis(phenylthio)acetals (8).An alternative path to the α-phenylthiosilanes (2) was to reduce the corresponding α-phenylsulphonylsilane (15); these, in turn, being readily available from alkylation or silylation of α-sulphonyl anions.The α-phenylthiosilanes (2) were converted into the O-trimethylsilylphenylthioacetal (18) by the sila-Pummerer rearrangement, although this was complicated by vinyl sulphide (20) formation in certain cases.Subsequent hydrolysis of (18) and (20) gave the ketone (3).