23063-31-2Relevant academic research and scientific papers
Silver-Catalyzed [2+1] Cyclopropenation of Alkynes with Unstable Diazoalkanes: N-Nosylhydrazones as Room-Temperature Decomposable Diazo Surrogates
Liu, Zhaohong,Li, Qiangqiang,Liao, Peiqiu,Bi, Xihe
supporting information, p. 4756 - 4760 (2017/04/14)
The [2+1] cycloaddition of alkynes with diazo compounds represents one of the most powerful and reliable methods for the construction of cyclopropenes. However, it remains a formidable challenge to accomplish the cyclopropenation of alkynes with non-stabilized diazoalkanes, owing to the fact that such compounds are unstable and prone to detonation. Herein, we report a general silver-catalyzed cyclopropenation reaction of alkynes with unstable diazoalkanes, by for the first time the discovery and application of N-nosylhydrazones as room-temperature decomposiable diazo surrogates. This method allows for the efficient assembly a wide variety of cyclopropene derivatives that are otherwise difficult to access by conventional methods.
Generation and stereoselective transformations of 3-phenylcyclopropene
Sheshenev, Andrey E.,Baird, Mark S.,Croft, Anna K.,Bolesov, Ivan G.
experimental part, p. 10036 - 10046 (2010/02/27)
A convenient and inexpensive approach to the generation of 3-phenylcyclopropenes is described. Reaction of these compounds with a range of dienophiles and dipolarophiles led to the stereoselective formation of [4+2]- and [3+2]-cycloadducts, which were exclusively exo-3-phenyl-cis-1,2-disubstituted cyclopropanes. Efficient trapping of 1-lithio-3-phenylcyclopropene with different electrophiles is also discussed. Ab initio calculations suggest that the lowest energy conformation of 3-phenylcyclopropene has the plane of the benzene ring perpendicular to the cyclopropene π-bond but with a low rotation barrier.
CONFORMATIONAL BEHAVIOUR OF 3-PHENYL- AND 3-CARBOMETHOXY-SUBSTITUTED CYCLOPROPENE DERIVATIVES
Domnin, I. N.,Kopf, J.,Keyaniyan, S.,Meijere, de A.
, p. 5377 - 5382 (2007/10/02)
According to MNDO calculated heats of formation for various 3-substituted cyclopropenes the ?-acceptor methoxycarbonyl as well as the ?-donor group phenyl both prefer a non-bisected orientation with respect to the three-membered ring.Temperature dependent
