99647-67-3Relevant academic research and scientific papers
Amide-Group-Directed Protonolysis of Cyclopropane: An Approach to 2,2-Disubstituted Pyrrolidines
Skvorcova, Marija,Jirgensons, Aigars
, p. 2478 - 2481 (2017/05/24)
Regioselective protonolytic C-C bond cleavage of acylated aminomethyl cyclopropanes can be achieved using trifluoroacetic acid. The intermediate tertiary carbenium ion undergoes an intramolecular amination to give 2,2-substituted pyrrolidines. The strength of the acid and the amine substituent are important factors to achieve high regioselectivity, suggesting intramolecular proton transfer from the protonated amide function. Preliminary mechanistic studies revealed that cyclopropane cleavage proceeds with retention of configuration at the carbon to which the proton is attached. This observation is consistent with the "edge" protonation trajectory of the C-C bond.
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.
Cyclopropanoid cyanoesters and method of making same
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, (2008/06/13)
Cyclopropanoid cyanoesters of the formula: STR1 where R' is --CH3 or --CH2 CH3, and A is (a) --H, or (b) A, B represents an aliphatic group joined to a carbon atom on the cyclopropanoid ring, thereby forming a spiro group, A, B being selected from structures having the formula: (i) --(CH2)n --, wherein n=3, 4, or 5, and (ii) --(CH2)2 --Y--(CH2)2 --, wherein Y is NCH3, O, or S); and, when A is --H, B is selected from the group consisting of: STR2 are disclosed. These compositions are useful in the synthesis of pyrethroids. A process for synthesis of cyclopropanoid cyanoesters by reacting 2-nitropropane with cyanoesters of the general formula: STR3 is also disclosed and claimed.
A TANDEM MICHAEL REACTION-CYCLOALKYLATION UTILIZING 2-NITROPROPANE: A FACILE ROUTE TO THE ACID COMPONENT OF INSECTICIDAL PYRETHROIDS
Babler, James H.,Spina, Kenneth P.
, p. 1923 - 1926 (2007/10/02)
Treatment of three representative β-substituted-α-cyanoacrylates (2) with 2-nitropropane and potassium carbonate in refluxing ethanol afforded stereoselectively cyclopropanoid precursors (4) to 3-substituted-2,2-dimethylcyclopropanecarboxylic acids (7).
