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cis/trans ‐ozonides of cycloolefins
Author(s) -
Griesbaum Karl,
Ball Volker,
Beck Johannes,
McCullough Kevin
Publication year - 1995
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.1995199511279
Subject(s) - chemistry , ozonide , pentane , ring (chemistry) , cis–trans isomerism , medicinal chemistry , stereochemistry , ozonolysis , organic chemistry
Ozonolyses in pentane of the unsubstituted cycloolefins having eleven‐, twelve‐, fourteen‐ and sixteen‐membered rings ( 1b‐e ) and of cyclohexadecen‐8‐one ( 12 ) gave the corresponding cis ‐ ( 2b‐e ; cis ‐ 15a ) and trans ‐ozonides ( 3b‐e ; trans ‐ 15a ), whereas cyclodecene ( 1a ) gave only the corresponding cis ‐ozonide ( 2a ). Ozonolyses on polyethylene of the dimethyl‐substituted cycloolefins bearing fourteen‐ and sixteen‐membered rings ( 7b, c ) also afforded cis ‐ and trans ‐isomeric ozonides ( 8, 9 ), whereas from the twelve‐membered ring ( 7a ) only the corresponding cis ‐ozonide ( 8a ) was formed.