Ozonolytic cleavage of cycloalkenes to terminally differentiated products

✍ Scribed by Stuart L. Schreiber; Ronald E. Claus; Jeff Reagan

• Book ID: 104221171
• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 247 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87729-1

✦ Synopsis

Conditions are reported which convert cycloalkenes to terminally dlfferentlated products through the intermediacy of a-alkoxy hydroperoxides. The ozonolytic cleavage of cycloalkenes in the presence of an alcohol affords a chain with an aldehyde and an a-alkoxy hydroperoxlde at the terminl. 2 We report that simple modlfications of ozonolytic workup procedures on these peroxides give rise to a variety of products with differentiated terminal functionality. Scheme 1 /-CHO /--CHO (c"z), Aso ) ~CH(OR)OOH Lt3N 2 4 /-CH(oR),