904689-49-2Relevant academic research and scientific papers
Neighbouring-group influence on the ring opening of some 2-alkyl-1,1,2-tribromocyclopropanes under phase-transfer conditions
Sydnes, Leiv K.,Alnes, Karl F. S.,Erdogan, Natalia
, p. 1737 - 1749 (2005)
Several 2-alkyl-1,1,2-tribromocyclopropanes were treated with sodium hydroxide and ethanol under phase-transfer conditions. Ring opening gave mixtures of the corresponding acetylenic diethyl ketals and acetals. When the steric bulk of the alkyl substituent was increased acetal formation dominated, and in the case of 1,1,2-tribromo-2-(tert-butyl)cyclopropane, the acetal was formed as the only product. Springer-Verlag 2005.
Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate
Mizoguchi, Haruki,Seriu, Masaya,Sakakura, Akira
supporting information, p. 15545 - 15548 (2020/12/30)
A procedure converting tribromocyclopropane to densely functionalized β-selenocyclopropylboronic ester using the 1,2-metallate rearrangement of a boron ate-complex has been developed. Treatment of an in situ-generated cyclopropenylboronic ester ate-complex with phenylselenenyl chloride triggered stereospecific rearrangement to produce functionalized cyclopropanes. DFT calculations for 1,2-metallate rearrangement suggested that the reaction proceeds through a seleniranium intermediate. This journal is
Brook Rearrangement as Trigger for Carbene Generation: Synthesis of Stereodefined and Fully Substituted Cyclobutenes
Zhang, Fa-Guang,Marek, Ilan
supporting information, p. 8364 - 8370 (2017/06/28)
Through a sequence that can be performed in a single vessel, involving regio- and diastereoselective copper-catalyzed carbomagnesiation of cyclopropenes, reaction with acylsilanes, and addition of THF as cosolvent, Brook rearrangement can be triggered to furnish a wide range of cyclobutenes with exceptional diastereoselectivity. Accordingly, stereodefined and highly substituted cyclobutenes with contiguous quaternary carbon centers can be synthesized easily and in high yield. The new strategy constitutes an unprecedented application of Brook rearrangement, one which involves the intermediacy of carbene species.
Rapid access to cyclopentadiene derivatives through gold-catalyzed cycloisomerization of ynamides with cyclopropenes by preferential activation of alkenes over alkynes
Cheng, Xing,Zhu, Lei,Lin, Meijun,Chen, Jianxin,Huang, Xueliang
supporting information, p. 3745 - 3748 (2017/04/03)
In this communication, gold-catalyzed intermolecular cycloisomerization of cyclopropenes and ynamides is investigated. The current transformation displayed an activation priority of double bonds over triple bonds by the cationic gold catalyst, giving the corresponding cyclopentadienes in good to excellent yields. Additionally, this protocol can be expanded to a one-pot two-step procedure for the synthesis of substituted cyclopentanones.
Cyclopropenylcarbinol derivatives as new versatile intermediates in organic synthesis: Application to the formation of enantiomerically pure alkylidenecyclopropane derivatives
Simaan, Samah,Masarwa, Ahmad,Zohar, Elinor,Stanger, Amnon,Bertus, Philippe,Marek, Ilan
scheme or table, p. 8449 - 8464 (2010/06/15)
The copper-catalyzed carbomagnesiation (or hydrometalation) reaction of chiral cyclopropenylcarbinol derivatives, obtained by means of a kinetic resolution of secondary allylic alcohols, leads to an easy and straightforward preparation of enantiomerically
Stable ethylene inhibiting compounds and methods for their preparation
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Page 7, (2008/06/13)
A method to inhibit the ethylene response in plants with cyclopropene compounds by first generating stable cyclopropane precursor compounds and then converting these compounds to the gaseous cyclopropene antagonist compound by use of a reducing or nucleophilic agent.
