89656-96-2Relevant academic research and scientific papers
Synthesis of Alkenes via Peterson Reaction
Ager, David J.
, p. 183 - 194 (2007/10/02)
The α-phenylthiosilanes (2) have been used to prepare the α-silyl anions (1) by reaction with lithium naphthalenide; subsequent condensation with a carbonyl compound gave the alkene (8) via the Peterson reaction.The α-phenylthiosilanes (2) were prepared from n,n-bis(phenylthio)acetals (4) by reaction with lithium naphthalenide and chlorotrimethylsilane.The n,n-bis(phenylthio)acetals (4) were obtained, in turn, from 1,1-bis(phenylthio)acetals (5) by anion formation with butyl-lithium-N,N,N',N'-tetramethylethylenediamine complex in hexane followed by reaction with an alkyl halide.The Peterson reaction was also used to prepare vinyl sulphides (9) and vinyl sulphones (13).
The Synthesis of Ketones via α-Silyl Sulphides
Ager, David J.
, p. 195 - 204 (2007/10/02)
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).
A General Procedure for Preparing α-Lithiosilanes. Generalization of the Peterson Olefination
Cohen, Theodore,Sherbine, James P.,Matz, James R.,Hutchins, Robert R.,McHenry, Barry M.,Willey, Paul R.
, p. 3245 - 3252 (2007/10/02)
A particularly convenient method for the preparation of α-lithiosilanes consists of the reductive lithiation of diphenyl thioacetals or thioketals with lithium 1-(dimethylamino)naphthalenide, treatment of the resulting anion with trimethylsilyl chloride,
Reactions of α-Silylsulphones
Ager, David J.
, p. 486 - 488 (2007/10/02)
α-Silylsulphones have been utilised to prepare vinylsulphones via the Peterson reaction and ketones by alkylation, reduction, and sila-Pummerer rearrangement.
