“…Whereas the deprotection of compounds 22 and 23 to give, respectively, ketones 39 and 40 was relatively fast (less than 10 h), derivatives 3 and 37 required longer reaction times (48 h) and more HgCl 2 and CaCO 3 to produce aldehyde 38 and diketone 41 (Method A, Scheme ). We could realize efficiently the bis(dimethylthio)ketal/bis(dimethyl)ketal interchange in compounds 22 and 23 by using HgCl 2 and HgO in methanol, generating 42 and 43 in excellent yields. 1 Transformations of Some Dithioacetal Compounds…”
The reaction of 2-picoline at the methyl group with NDA and KDA followed by dimethyldisulfide trapping furnished, respectively, dithioacetals and trithioortho esters with high selectivity. The method was successfully applied to other methyl-substituted pyridines, quinolines, and pyrazines. Dithioketals were prepared by a one-pot procedure involving the reaction of metalated 2-picoline with 2 equiv of dimethyldisulfide followed by in situ trapping with a second electrophile. All of the generated thio-substituted compounds were efficiently transformed in presence of mercury salts or under oxidizing conditions to other functional groups comprising aldehydes, ketones, ketals, thiol esters, orthoesters, and esters.
“…Whereas the deprotection of compounds 22 and 23 to give, respectively, ketones 39 and 40 was relatively fast (less than 10 h), derivatives 3 and 37 required longer reaction times (48 h) and more HgCl 2 and CaCO 3 to produce aldehyde 38 and diketone 41 (Method A, Scheme ). We could realize efficiently the bis(dimethylthio)ketal/bis(dimethyl)ketal interchange in compounds 22 and 23 by using HgCl 2 and HgO in methanol, generating 42 and 43 in excellent yields. 1 Transformations of Some Dithioacetal Compounds…”
The reaction of 2-picoline at the methyl group with NDA and KDA followed by dimethyldisulfide trapping furnished, respectively, dithioacetals and trithioortho esters with high selectivity. The method was successfully applied to other methyl-substituted pyridines, quinolines, and pyrazines. Dithioketals were prepared by a one-pot procedure involving the reaction of metalated 2-picoline with 2 equiv of dimethyldisulfide followed by in situ trapping with a second electrophile. All of the generated thio-substituted compounds were efficiently transformed in presence of mercury salts or under oxidizing conditions to other functional groups comprising aldehydes, ketones, ketals, thiol esters, orthoesters, and esters.
“…I~ We have reported the formation of 3,5,5-trimethyl-2oxomorpholin-3-yl (l), an aminocarboxy capto-dative radical, upon dissolution of meso-and dl-bi (3,5,5-trimethyl-2-oxomorpholin-3-yl) (2a and 2b).4 In chloroform Spectra were observed in the absence of oxygen at 60 "C in chloroform solvent. The corresponding Linnett structures have a double/quartet of electrons for each atom with favorable p01arization.l~ Schleyer and co-workers have calculated the electronic stabilization attributed solely to the captodative effect to be 3 kcal/mol for the aminocyano-substituted carbon radical and 10 kcal/mol for the aminoboron-substituted radi~a1.…”
Photolysis of 4-Carbomethoxy-JV-methylphthalimide (21d) and 1-Hexene. Photolysis by the general procedure gave a pair of products characterized as 23d and 24d in a 27:73 ratio in 46% yield. Pure compound 24d: mp 118-119 °C NMR (CDC13) 3.01 (m, 2 H), 3.25 (s, 3 ), 3.71 (m, 2 H), 3.96 (s, 3 ), 7.70 (d, 1 H,
“…The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give a white solid. Recrystallization using a 10% ethyl acetate-hexane mixture yielded 194 mg of 4-phenyl-3-cyano-3-buten-2-one (26) (97%): mp 80-81 °C; IR (KBr) 2210,1700,1600,1370,1250,1200, 970, and 990 cm"1; NMR (CDC13, 90 MHz) 2.3 (s, 3 ), 7.15-7.3 (m, 3 H), 7.6-7.8 (m, 2 H), and 7.85 (s, 1H). Anal.…”
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