Organic sulfur compounds. VI. Reduction of three α-(o-nitrophenylthio)ketones with sodium borohydride

Abstract

Reduction of three α-(o-nitrophenylthio)ketones with sodium borohydride and palladium–charcoal gave mainly α-(o-nitrophenylthio)alcohols and, as minor products, α-(o-aminophenylthio)alcohols. Only two benzothiazines were formed. Bis[2-(3-phenyl-2H-1,4-benzothiazine)] was a minor product of the catalyzed reduction of ω-(o-nitrophenylthio)acetophenone whereas 1-(3,4-dihydro-4-hydroxy-3-oxo-2H-1,4-benzothiazin-2-yl)benzyl alcohol was the main product of the catalyzed reduction of α-benzoyl-α-(o-nitrophenylthio)acetate.

Polystyrene‐Supported 1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene as an Efficient and Reusable Catalyst for the Thiolysis of 1,2‐Epoxides under Solvent‐Free Conditions

“…Column chromatography was performed by using silica gel 230-400 mesh and eluting as reported in the following characterization data. Hydroxy sulfides 3aA, [11e] 3aB, [14] 4aA, [15] 4aB, [16] are known compounds; while 3aC, [17] 3aD, [18] 3aE, [5g] 3eC, [19] 4aC, [17,20] 4aD, [19] 4aE, [21] have already been prepared, but spectroscopic data have not been reported or are not complete to the best of our knowledge. Compounds 3eE, 4bC, 4bE, 4cC, 4cE, 4dC, 4dE, are new compounds.…”

“…13 C NMR (CDCl 3 , 100.6 MHz): δ = 33. 9, 51.3, 65.5, 117.5, 127.6, 128.2, 128.6, 134.0, 139.4 -1-ol (3eC) 3, 26.1, 32.9, 34.2, 56.8, 72.5, 115.4, 115.5, 118.9, 130.4, 138.1, 149. (20), 125 (100), 93 (12), 80 (18). C 12 H 17 NOS (223.3): calcd.…”

“…C 64.53,H 7.67,N,6.27;found C 64.44,H 7.58,N 6.30. 2-(Allylthio)cyclohexan-1-ol (3eE) 24.0, 25.7, 32.4, 33.3, 33.6, 51.8, 72.1, 116.6, 134.6 (17), 98 (62), 81 (100), 69 (28), 57 (20). C 9 H 16 OS (172.3): calcd.…”