91787-21-2Relevant academic research and scientific papers
Integrated Chemical Process: One-Pot Double Elimination Method for Acetylenes
Orita, Akihiro,Yoshioka, Naonori,Struwe, Petra,Braier, Arnold,Beckmann, Anke,Otera, Junzo
, p. 1355 - 1363 (2007/10/03)
A novel one-pot process for synthesis of acetylenes has been achieved in which the following series of steps are integrated: addition of an α-anion of sulfone to aldehyde; trapping of the resulting adduct to incorporate a leaving group, and double elimination of this intermediate. Consolidation of Peterson elimination renders the process much simpler. This method provides a convenient and high-yielding access to a variety of enynes and polyynes as well as to functionally substituted aryl acetylenes containing halogen(s) or acetal groups, which are useful building blocks for aryl acetylene scaffolds. Iteration of the one-pot generation of acetylenic bonds provides a new metodology for the buildup of aryl acetylene skeletons.
Integrated chemical process. One-pot preparation of acetylenes by Peterson-sulfone elimination
Orita, Akihiro,Yoshioka, Naonori,Otera, Junzo
, p. 1023 - 1024 (2007/10/03)
Integration of silylation of α-sulfonyl carbanion, addition of the anion of the resulting α-silyl sulfone to aldehyde, Peterson elimination, and sulfone elimination leads to one-pot synthesis of acetylenes.
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).
