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Unsaturated Ozonides from the Ozonolysis of Cyclodienes in the Presence of Carbonyl Compounds
Author(s) -
Park Shin Hee,
Lee Joo Yeon,
Huh Tae Sung
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200108)2001:16<3083::aid-ejoc3083>3.0.co;2-k
Subject(s) - ozonolysis , chemistry , dichloromethane , ozone , conjugated system , organic chemistry , medicinal chemistry , solvent , polymer
Treatment of the conjugated C 5 ‐ to C 8 ‐cyclodienes ( 5a − 5b ) with one molar equivalent of ozone in dichloromethane in the presence of added carbonyl compounds ( 3 ) resulted almost exclusively in monoozonolysis reactions to give the corresponding unsaturated cross‐ozonides 8 and/or 10 as the major products. In contrast, ozonolysis of the nonconjugated olefins 1,5‐cyclooctadiene ( 6a ) and 1,5‐dimethyl‐1,5‐cyclooctadiene ( 6b ) under similar conditions afforded both unsaturated cross‐ozonides ( 11 and 17 , respectively) derived from monoozonolysis and cross‐ozonides ( 12 + 16 and 19 , respectively) derived from diozonolysis.