53627-10-4Relevant academic research and scientific papers
Trichloromethanesulfonyl chloride: A chlorinating reagent for aldehydes
Jimeno, Ciril,Cao, Lidong,Renaud, Philippe
, p. 1251 - 1255 (2016/02/19)
Trichloromethanesulfonyl chloride (CCl3SO2Cl), a commercially available reagent, has been found to perform efficiently in the α-chlorination of aldehydes, including its catalytic asymmetric version, under very mild reaction conditions. Under our reaction conditions, this compound outperforms typical chlorinating reagents for organic synthesis, facilitates workup and purification of the product, and minimizes the formation of toxic, chlorinated organic waste.
Stereocontrolled 1,3-phosphatyloxy and 1,3-halogen migration relay toward highly functionalized 1,3-dienes
Kazem Shiroodi, Roohollah,Dudnik, Alexander S.,Gevorgyan, Vladimir
supporting information; experimental part, p. 6928 - 6931 (2012/06/15)
A double migratory cascade reaction of α-halogen-substituted propargylic phosphates to produce highly functionalized 1,3-dienes has been developed. This transformation features 1,3-phosphatyloxy group migration followed by 1,3-shifts of bromine and chlorine as well as the unprecedented 1,3-migration of iodine. The reaction is stereodivergent: (Z)-1,3-dienes are formed in the presence of a copper catalyst, whereas gold-catalyzed reactions exhibit inverted stereoselectivity, producing the corresponding E products.
Synthesis of 1,1-bisphosphono-2-aza-1,3-dienes, a new class of electron-deficient azadienes
Masschelein, Kurt G.R.,Stevens, Christian V.
, p. 4336 - 4338 (2008/09/21)
1,1-Bisphosphono-2-aza-1,3-dienes are formed by 1,4-dehydrohalogenation of the corresponding N-(bisphosphonomethyl)-α-haloimines in moderate to good yields. The precursors could be formed by condensation of bisphosphono-amines and the corresponding α-haloaldehydes.
The Regiochemistry of the Radical Addition of N-Chloroamides to Enol Ethers
Caron, Gilles,Lessard, Jean
, p. 8039 - 8058 (2007/10/02)
The orientation of the radical addition of N-chloroamides (ZCONHCl) to enol ethers was studied as a function of Z and the enol ether structure and compared with the orientation of radical addition of thioacetic acid and the orientation of typical electrop
Regeneration of α-haloaldehydes from α-halodimethylacetals
Boni,Ghelfi,Pagnoni,Pinetti
, p. 1915 - 1921 (2007/10/02)
α-Chlorodimethylacetals are hydrolysed in a mixture of acetic acid and aq.HCl (3.5 M) to α-chloroaldehydes in excellent yields. On replacing HCl by HBr the same procedure is applied to α-bromodimethylacetals.
