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Manganese(III)‐mediated free‐radical cyclization of acitve methylene compounds, alkenes and molecular oxygen. Syntheses of sulfur‐ and phosphorus‐containing 1,2‐dioxan‐3‐ols
Author(s) -
Qian ChangYi,
Nishino Hiroshi,
Kurosawa Kazu
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300136
Subject(s) - chemistry , manganese , phosphinate , sulfur , methylene , sulfoxide , medicinal chemistry , oxygen , molecular oxygen , phosphorus , organic chemistry , sulfone , fire retardant
The reactions of β‐keto sulfoxide, β‐keto sulfones, or β‐keto phosphinate with 1,1‐disubstituted ethenes in the presence of manganese(III) acetate and molecular oxygen yielded 4‐phenylsulfinyl‐, 4‐phenylsulfonyl‐, or 4‐phosphinoyl‐1,2‐dioxan‐3‐ols 3 in moderate‐to‐good yields. m ‐Chloroperbenzoic acid oxidation of 4‐phenylsulfinyl‐1,2‐dioxan‐3‐ols gave the corresponding 4‐phenylsulfonyl derivatives. The temperature dependence of the reactions was observed and the stereochemistry of the 1,2‐dioxan‐3‐ols are discussed.