76200-39-0Relevant academic research and scientific papers
A Michael Addition and Peterson Olefination Sequence Using 1-Silylethenyl Sulfides and Sulfoxide
Kanemasa, Shuji,Kobayashi, Hiroshi,Tanaka, Junji,Tsuge, Otohiko
, p. 3957 - 3964 (2007/10/02)
Reaction of organolithiums with a 1-(trimethylsilyl)ethenyl sulfide produces 1,2-bis(trimethylsilyl)-cyclopropanes, while use of 1-silylethenyl sulfides bearing a bulkier silyl moiety results in exclusive formation of the corresponding Michael adducts anions which are then quenched with aldehydes to give vinyl sulfides.On the contrary, a 1-(trimethylsilyl)ethenyl sulfoxide undergoes smooth Michael addition with a variety of organometallics and the resulting carbanion intermediates can be quenched with aldehydes to produce vinyl sulfoxides.Scope and limitations of these sequential reactions are discussed.
Synthesis of Aldehydes from Phenylthiotrimethylsilylmethane
Ager, David J.
, p. 1131 - 1136 (2007/10/02)
Phenylthiotrimethylsilylmethyl-lithium (4) reacts with alkyl halides to give 1-phenylthio-1-trimethylsilylalkanes (5), which can also be prepared by the addition of alkyl-lithium to 1-phenylthio-1-trimethylsilylethene (8), or from bis(phenylthio)acetals (11).The 1-phenylthio-1-trimethylsilylalkanes (5) can be converted into the corresponding aldehyde (15) by oxidation to the sulphoxide (13), thermal rearrangement, and hydrolysis of the resultant O-silyl thioacetal (14).
ALDEHYDES FROM ALKYLLITHIUMS WITH 2-CARBON HOMOLOGATION
Ager, David J.
, p. 587 - 590 (2007/10/02)
1-Phenylthio-trimethylsilylalkanes, which are readily converted to aldehydes, are prepared by the addition of alkyllithiums to phenylthioethene, trimethylsilylethene and 1-phenylthio-1-trimethylsilylethene.
A NEW METHOD FOR PREPARING 1-PHENYLTHIO-1-TRIMETHYLSILYLALKANES: THE PREPARATION OF α-SILYLCARBANIONS AND OLEFINS.
Ager, David J.
, p. 2923 - 2926 (2007/10/02)
1-Phenylthio-1-trimethylsilylalkanes(1) are prepared in high yield from 1,1-bis(phenylthio)acetals(2) by reaction with lithium naphthalenide(3) followed by chlorotrimethylsilane. α-Silylcarbanions are formed from the alkanes(1) and lithium naphthalenide(3).Subsequent reaction with carbonyl compounds gave the olefins(4) via the Peterson reaction.
A NEW METHOD FOR CONVERTING ALKYL HALIDES TO HOMOLOGOUS ALDEHYDES
Ager, David J.,Cookson, Richard C.
, p. 1677 - 1680 (2007/10/02)
Phenylthiotrimethylsilylmethyl lithium can be alkylated and the product hydrolysed to the aldehydes by oxidation and rearrangement.
