On alleged norbornadien -7-ones.

✍ Scribed by Shay Yankelevich; Benzion Fuchs

• Publisher: Elsevier Science
• Year: 1967
• Tongue: French
• Weight: 303 KB
• Volume: 8
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)89943-3

✦ Synopsis

Since we had recently studied (1) the photolysis of certain substituted norbornen-T-ones, we decided to investigate the norbornadien-T-one system I. While there is no a priori reason why this system should not exist, it seems to be a particularly elusive one. Thus the Diels-Alder addition of acetylenes to substituted cyclopentadienones, instead of giving the expected norbornadien -T-ones yields the aromatic products, via decarbonylation (2). Acid hydrolysis of the ketal derivatives of I (3) likewise leads to spontaneous decarbonylation. Although the literature describes several substituted norbornadien -T-ones, our results show that most of these assignments are incorrect. The synthesis of P-phenylnorbornadien -T-one II has been reported (4), albeit in very small yield. The substance exhibited I.R. &sorption, vm_.(C*)

1730 cm-l, melted at 135" (d) and decarbonylated at even higher