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Functionalized Ozonides by Substitution Reactions of Chlorinated Ozonides with Difunctional Alcohols
Author(s) -
Griesbaum Karl,
Quinkert RalfOlaf
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971225
Subject(s) - ozonide , chemistry , diastereomer , ozonolysis , alcohol , ozone , substitution (logic) , medicinal chemistry , substitution reaction , organic chemistry , computer science , programming language
Substitution of 3‐chloro‐3,5‐bis(chloromethyl)‐5‐methyl‐1,2,4‐trioxolane ( 3 ) with allyl alcohol gave the corresponding diastereomeric allyloxy‐substituted ozonides 4 , which were converted into diozonides 7 by ozone treatment. Substitutions of 3 with ethanediol or with 1,3‐propanediol gave the corresponding hydroxyalkoxy‐substituted ozonides 8, 14 , which were oxidized to the corresponding aldehydes 10, 16 . Reaction of 3,5‐dichloro‐3,5‐bis(chloromethyl)‐1,2,4‐trioxolane ( 1a ) with ethanediol gave the corresponding bis(hydroxy)‐substituted ozonide 19 as well as a bicyclic ozonide 18 by reaction of 1a with ethanediol in a ratio of 1:1.