Studies on the becarbonylation and decarboxylation reactions of 5,6-epoxy-4,5-diphenyl-2-pyrone

✍ Scribed by Albert Padwa; Richard Hartman

• Book ID: 104211976
• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 186 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70253-x

✦ Synopsis

I& current general interest in the photochemistry of both epoxides* and cu-pyrones3 prompts us to disclose sane preliminary data concerning a nmber of unusual transformations of 5,6-epoxy-k,5-diphenyl-2-pyrone (I).4'5 Our results indicate that I is remarkably versatile in its reactions and may undergo various modes of decomposition depending on the particular experimental conditions employed. Thus treatment of I with concentrated sulfkric acid at 0' and then addition of the brown solution to water resulted in precipitation of k-hydroxy-3,4-diphenyl-crotonic acid-r-lactone (II) in 8@ yield, m.p. 152-153'. The unsaturated la&one was identical in all respects with an a authentic sample prepared by the method of Thiele. Treatment of I with sodium methoxide on the other hand readily afforded methyl desylacetate (IIIA) as the major product. 7 Elucidation of the strixtwe of IIIA was readily established on the basis of spectral evidence and ccxnparlson to authentic material independently synthesized.