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N‐p ‐toluenesulfonyl‐2‐oxazolidones Via the cycloaddition reaction of p ‐tolucnesulfonyl isocyanate and epoxides
Author(s) -
Herweh J. K.,
Kauffman W. J.
Publication year - 1971
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.5570080616
Subject(s) - chemistry , isocyanate , adduct , epoxide , ether , polymer chemistry , organic chemistry , bromide , medicinal chemistry , styrene , styrene oxide , cycloaddition , oxide , catalysis , copolymer , polymer , polyurethane
The reaction of styrene oxide and phenyl glycidyl ether with p ‐toluenesulfonyl isocyanate, employing a hydrocarbon‐soluble adduct of tributylphosphine oxide and lithium bromide as catalyst, results in excellent yields of the N‐p ‐toluenesulfonyl‐2‐oxazoIidones. The 5‐isomeric‐2‐oxazolidone is obtained from phenyl glycidyl ether, but in contrast to conventional isocyanates, the p ‐toluenesulfonyl isocyanate, upon reaction with styrene oxide, produces the 4‐isomeric 2‐oxazolidone as the major product. The effect of the N ‐sulfonyl group on the nmr spectra of 2‐oxazolidones is discussed.