Heterocycles p. 589 - 615 (1996)
Update date:2022-07-30
Topics:
Endo, Katsuya
Takahashi, Hiroyasu
Aihara, Minako
o-Hydroxymethylbenzyl alcohol and o-hydroxyethylbenzyl alcohols have been converted to phthalide and dihydroisocoumarins, very easily and in high yields, by oxidation with non-activated manganese dioxide. In contrast, the reaction of o-hydroxypropylbenzyl alcohol stopped at the aldehyde level, and afforded only a small amount of the corresponding lactone under the same condition. This implies that the first oxidation product, a benzaldehyde, could be oxidized further via a hemiacetal, but the second oxidation to lactone is very much dependent on the ability of stable intramolecular hemiacetal formation, and not on the intermolecular mode at all.
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Doi:10.1039/cc9960000313
(1996)Doi:10.1016/S0022-328X(96)06682-X
(1997)Doi:10.1055/s-1996-4195
(1996)Doi:10.1016/0040-4020(95)01099-8
(1996)Doi:10.1039/j39680001667
(1968)Doi:10.1055/s-1997-1506
(1997)