50299-81-5Relevant academic research and scientific papers
gem-Dimethylcyclopropanation using triisopropylsulfoxonium tetrafluoroborate: Scope and limitations
Edwards, Michael G.,Paxton, Richard J.,Pugh, David S.,Whitwood, Adrian C.,Taylor, Richard J. K.
experimental part, p. 3279 - 3288 (2009/05/11)
A new nucleophilic isopropyl transfer reagent, triisopropylsulfoxonium tetrafluoroborate, has been prepared and evaluated. Thus, using this reagent and NaH in DMF, a range of electron deficient alkenes, including several chalcone analogues, α,β-unsaturated ketones, dienones and quinones, plus α,β-unsaturated esters, nitrile, sulfone and nitro examples, have been converted into the corresponding gem-dimethylcyclopropane compounds.
An improved gem-dimethylcyclopropanation procedure using triisopropyl-sulfoxonium tetrafluoroborate
Edwards, Michael G.,Paxton, Richard J.,Pugh, David S.,Taylor, Richard J. K.
, p. 521 - 524 (2008/12/21)
A new procedure for the cyclopropanation of α,β-unsaturated carbonyl compounds and related systems is described which employs triisopropylsulfoxonium tetrafluoroborate and sodium hydride in dimethylformamide. Using this reagent, a range of α,β-unsaturated ketones (and an ester and a vinyl nitro example) has been converted into the corresponding gem-dimethylcyclopropyl carbonyl compounds; in addition, a preliminary result is described in which an activated alcohol is converted directly into a gem-dimethylcyclopropyl ketone by a one-pot tandem oxidation-cyclopropanation sequence, albeit in low yield. Georg Thieme Verlag Stuttgart.
Synthesis and photolysis behaviour of 2-(Δ1-pyrazolinyl)-Δ3(1,3,4) oxadiazolines. Application to the synthesis of gem-dimethylcyclopropane ketone
Lachheb, Jalel,Martin, Marie-Therese,Khemiss, Abdel-Kader
, p. 9029 - 9031 (2007/10/03)
The photolysis of 2-(Δ1-pyrazolinyl)-Δ3(1,3,4) oxadiazoline 5 led to exclusive formation of gem-dimethylcyclopropane ketone 6.
Synthesis and Chemistry of Azolenines. Part 16. Preparation of both 3H- and 2H-Pyrroles from 2,2-Disubstituted 1,4-Diketones via the Paal-Knorr Reaction, and Isolation of Intermediate 2-Hydroxy-3,4-dihydro-2H-pyrroles
Lui, Kon-Hung,Sammes, Michael P.
, p. 457 - 468 (2007/10/02)
Treatment of 2,2-disubstituted 1,4-diketones (1) with liquid ammonia gives high yields of isolable isomeric 2-hydroxy-3,4-dihydro-2H-pyrroles (10) and (11), many of which may be dehydrated to 3H-pyrroles (2) together, in certain cases, with isomeric methylene-pyrrolines (14) and (15).When heated in acetic acid with ammonium acetate, the diketones (1) yield 2H-pyrroles (18), sometimes in admixture with 3H-pyrroles (2) from which they are formed by rearrangement.The diketones (1), including some novel examples, are prepared from nitro-ketones (6) by the Nef reaction, as well as other methods.
Nitro Compounds as Nucleophilic Alkylidene Transfer Reagents
Ono, Noboru,Yanai, Tetsuya,Hamamoto, Isami,Kamimura, Akio,Kaji, Aritsune
, p. 2806 - 2807 (2007/10/02)
Nitro compounds can be used as useful and general nucleophilic alkylidene transfer reagents for the preparation of various cyclopropanes.
