Radical decarbonylation reactions I. Decarbonylation of 9-phenyl-9-fluorenylacetaldehyde

✍ Scribed by Bruno M. Vittimberga

• Book ID: 104223335
• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 207 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)90195-3

✦ Synopsis

Free radical rearrangement reactions have been the subject of a number of publications in recent years. Of the many reports that appear in the literature, few describe uncomplicated radical migrations that invalve simultaneous ring expansion. +1 We have examined the peroxide initiated decarbonylation of 9-phenyl-9-fluorenylacetaldehyde (I) and found that the decarbonylation was accompanied by a rather smooth conversion to 9-phenylphenanthrene (II). *1. During the latter stages of the preparation of this paper we learned that Brother H. Philip, F.S.C., Lewis College. Lockport. Illinois was also working on these systems. (Eighth Annual Report on Research Sponsored by the Petroleum Research Fund for the period ending August 31, 1963). In a private communication Brother Philip stated that he obtained substantially the same results as we did. Another reaction similar to the one described in this paper is the decarbonylation of (1-methylindanyl)acetaldehyde under free radical conditions to give 1. 1-dimethylindane and 2-methyltetraiin [J. W. Wilt and C. A. Schneider, J. Org. Chem. 26. 4196 (1961)].