2243-98-3Relevant articles and documents
Generation of Akylidenecarbenes by the Alkenation of Carbonyl Compounds with Lithiotrimethylsilyldiazomethane
Ohira, Susumu,Okai, Keiji,Moritani, Takanori
, p. 721 - 722 (1992)
The reaction of carbonyl compounds and lithiotrimethylsilyldiazomethane, which generate alkylidenecarbenes, gives a terminal acetylene from an aldehyde and cyclopentene derivatives from ketones.
A Sequential Homologation of Alkynes and Aldehydes for Chain Elongation with Optional 13C-Labeling
Brunner, Andreas,Hintermann, Lukas
, p. 2787 - 2792 (2016/02/27)
Terminal alkynes (RCCH) are homologated by a sequence of ruthenium-catalyzed anti-Markovnikov hydration of alkyne to aldehyde (RCH2CHO), followed by Bestmann-Ohira alkynylation of aldehyde to chain-elongated alkyne (RCH2CCH). Inverting the sequence by starting from aldehyde brings about the reciprocal homologation of aldehydes instead. The use of 13C-labeled Bestmann-Ohira reagent (dimethyl ((1-13C)-1-diazo-2-oxopropyl)phosphonate) for alkynylation provides straightforward access to singly or, through additional homologation, multiply 13C-labeled alkynes. The labeled alkynes serve as synthetic platform for accessing a multitude of specifically 13C-labeled products. Terminal alkynes with one or two 13C-labels in the alkyne unit have been submitted to alkyne-azide click reactions; the copper-catalyzed version (CuAAC) was found to display a regioselectivity of >50 000:1 for the 1,4- over the 1,5-triazine isomer, as shown analytically by 13C NMR spectroscopy.
Synthesis of acetylenes via dehydrobromination using solid anhydrous potassium phosphate as the base under phase-transfer conditions
Shenawi-Khalil, Sanaa,Sonavane, Sachin U.,Sasson, Yoel
experimental part, p. 2295 - 2297 (2012/07/27)
Phase-transfer catalyzed preparation of acetylenes from the corresponding vicinal dibromo compounds via double dehydrobromination using the mild solid base, anhydrous potassium phosphate, under very mild conditions is reported.
