10423-18-4Relevant academic research and scientific papers
Cycloadditions of Diazoalkanes to Enol Ethers Catalyzed by Chromium Complexes - The First Direct Spectroscopic Observation of a Carbene Complex Intermediate
Pfeiffer, Juergen,Doetz, Karl Heinz
, p. 2828 - 2830 (1997)
Keywords: carbene complexes; chromium; cyclopropanations; homogeneous catalysis
Hypervalent-iodine(iii) oxidation of hydrazones to diazo compounds and one-pot nickel(ii)-catalyzed cyclopropanation
Liu, Haixuan,Wei, Yunyang,Cai, Chun
, p. 674 - 678 (2016/01/12)
A one-pot process for the catalytic cyclopropanation of various alkenes with unsubstituted hydrazones is described. Iodosobenzene (Ph = O) was found to be a competent oxidant of hydrazones to diazo compounds. Ni(OH)2 was chosen as an effective and cheap metal catalyst. The cyclopropane products can be generated efficiently (5 min-4 h) in moderate to good yields (42-91%) under mild (80°C) and neat conditions.
Intermolecular metal-free cyclopropanation of alkenes using tosylhydrazones
Barluenga, Jose,Quinones, Noelia,Tomas-Gamasa, Maria,Cabal, Maria-Paz
supporting information; experimental part, p. 2312 - 2317 (2012/06/01)
We describe the first general method for the metal-free cyclopropanation of alkenes by using N-tosylhydrazones as an in situ source of diazo compounds. This new method works with a wide variety of alkenes (styrene derivatives, dienes, enynes, and electron-deficient alkenes) by using N-tosylhydrazones derived from various ketones or aldehydes (aromatic, aliphatic, enones). The reaction is performed with the use of K2CO3 as a base to form the diazo species and is compatible with a wide array of functional groups. A new procedure for the synthesis of cyclopropanes by the formal cyclopropanation of carbonyl compounds and alkenes is described. This metal-free reaction proceeds through the base-promoted decomposition of tosylhydrazones. There is significant tolerance of the functional groups, enabling cyclopropanation in the presence of functionalities often not compatible with other methodologies.
Chromium complex catalyzed synthesis of spirocyclopropanes from diaryl diazo compounds - Direct NMR-spectroscopic observation of a carbene complex intermediate
Pfeiffer, Juergen,Nieger, Martin,Doetz, Karl Heinz
, p. 1011 - 1022 (2007/10/03)
The [2 + 1] cycloaddition reaction of electron-rich alkenes such as enol ethers with 9-diazo-9H-fluorene (1) is efficiently catalyzed by pentacarbonyl(η2-cis-cyclooctene)chromium(0) (2). This cyclopropanation reaction shows a pronounced prefere
3,6-Dimethoxyfluorenylidene: A Ground-State Singlet Carbene
Chuang, Carl,Lapin, Stephen C.,Schrock, Alan K.,Schuster, Gary B.
, p. 4238 - 4243 (2007/10/02)
Irradiation of 3,6-dimethoxy-9-diazofluorene gives 3,6-dimethoxy-9-fluorenylidene.This carbene was detected in frozen media by low-temperature optical spectroscopy and at room temperature in fluid solution by nanosecond laser techniques.The EPR spectrum o
CHEMICAL AND PHYSICAL PROPERTIES OF FLUORENYLIDENE: EQUILIBRATION OF THE SINGLET AND TRIPLET CARBENES.
Grasse,Brauer,Zupancic,Kaufmann,Schuster
, p. 6833 - 6845 (2007/10/02)
Irradiation of 9-diazofluorene, with a pulsed laser on a picosecond or nanosecond time scale at room temperature, or at 10 K in a glassy matrix, gives detectable fluorenylidene. This species is shown to exist, under most experimental conditions, as a rapi
