✍ Scribed by Paul Müller; Jacky Blanc
No coin nor oath required. For personal study only.
The C,C‐bond cleavage which occurs during chromic acid oxidation of t‐butylphenylmethanol (1) and 1,2‐diphenylethanol (2) to the extent of up to 67% is reduced to 3% for 1 and 13% for 2 when the reaction is run in acetone, and totally suppressed upon co‐oxidation of the alcohols 1 and 2 with oxalic acid. Similarly, the yield of 7‐norbornanone obtained from 7‐norbornanol (7) is raised in going from acetic acid (24%) to acetone (41%) and approaches 100% in the co‐oxidation. With the co‐oxidation 5‐endo‐bicyclo [2.1.1]hexanol (3) is converted to the corresponding ketone in 54% yield. Mechanistic implications of these results are discussed.
📜 SIMILAR VOLUMES
## Abstract The structures of 4‐hydroxy‐3,5,6‐trichloropyridine‐2‐carboxylic acid (1a) and 6‐hydroxy‐3,4,5‐trichloro‐2‐carboxylic acid (1b) were verified by the NMR analysis of their corresponding methylated and decarboxylated derivatives 2,3,5‐trichloro‐4‐methoxypyridine (5) and 3,4,5‐trichloro‐2‐
The inÑuence of hydrogen bonding (HB) on the 13C chemical shift tensors in four solid amino acids was studied by the ab initio gauge-included atomic orbital (GIAO) approach. The results of the present calculations were compared with those predicted previously and with the experimentally observed shi
An investigation of the kinetics of oxidation of epimeric piperidin-4-ols, oxan-4-ols, and cyclohexanol by N-chloro-r-2, c-6-diphenyl-t-3-methylpiperidin-4-one (NCP) in aqueous acetic acid in the presence of perchloric acid shows that the reaction is first-order each in substrate and oxidant. Both H