13131-74-3Relevant academic research and scientific papers
Reductive Chlorination and Bromination of Ketones via Trityl Hydrazones
Reyes, Julius R.,Rawal, Viresh H.
, p. 3077 - 3080 (2016)
A method is presented for the direct transformation of a ketone to the corresponding reduced alkyl chloride or bromide. The process involves the reaction of a ketone trityl hydrazone with tBuOCl to give a diazene which readily collapses to the α-chlorocar
Simple, chemoselective hydrogenation with thermodynamic stereocontrol
Iwasaki, Kotaro,Wan, Kanny K.,Oppedisano, Alberto,Crossley, Steven W. M.,Shenvi, Ryan A.
supporting information, p. 1300 - 1303 (2014/02/14)
Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.
REACTIONS OF o-(N-METHYLCARBAMOYL)PHENYL SULPHOXIDES WITH ELECTROPHILES
Uchida, Yuzuru,Oae, Shigeru
, p. 649 - 654 (2007/10/02)
Reactions of alkyl o-(N-methylcarbamoyl)phenyl sulphoxides 1 with various electrophiles, such as acetic anhydride, acetyl chloride, thionyl chloride and p-toluenesulphonyl chloride, have been carried out.Treatment of 1 with excess acetic anhydride in general leads to the formation of the Pummerer type rearrangement products or related products.In the reactions of 1 with acetyl, thionyl and p-toluenesulphonyl chlorides, 2-methyl-1,2-benzisothiazole-3(2H)-one, 4b, and alkyl chlorides were obtained nearly quantitatively.All these reactions can be rationalized on the basis of the initial O-acylation and subsequent either α-proton removal to result in the Pummerer rearrangement or nucleophilic attack of neighbouring carbamoyl group to afford the five-membered products 4b.
Reactions of Cyclohexenyl Halides with Tributylstannane. Stereoelectronic Effects on SH2 Reactions at Halogen
Beckwith, Athelstan L. J.,Westwood, Steven W.
, p. 2123 - 2132 (2007/10/02)
Allylic halogenation of t-butylcyclohexene (2a) with t-butyl hypochlorite or N-bromosuccinimide affords mixtures containing mainly trans-5-t-butyl-3-chlorocyclohexene (2b) and the corresponding trans bromo compound (2c) respectively.The copper-catalysed r
Nucleophilic Substitution and Competing Elimination in Cyclohexane and Steroid Reactions. A Comparison of Experiments and Force Field Calculations including the Regioselectivity of Steroid Eliminations
Gschwendtner, W.,Hoppen, V.,Schneider, H.-J.
, p. 1201 - 1226 (2007/10/02)
A number of nucleophilic replacements including hydroxyl group substitutions are reported which show clean inversion with 3β-substituted cholestanes, whereas comparable cyclohexanes yield largely olefinic byproducts.Model calculations with the MM1 molecular mechanics force field demonstrate that twist boot intermediates as proposed in the literature for cyclohexane eliminations will require significantly higher strain energy in the steroid only if the interaction of both leaving group and attacking agent at Cβ-H is included.The predominance of Δ2 over Δ3 products in the steroid eliminations is based less on steric energy differences of these olefins, than on those of the preceding transition states.For the steroid all-chair ground state MM1, MM2 and crystal structure results are found to be in agreement.The calculations show the absence of conformational transmission of the A-ring twist-boat distortions in the C and D rings.
