Strained systems. VI. Some reactions of 5,6-diphenyltricyclo-[2.1.1.o5,6]hexan-2-one

✍ Scribed by Satoru Masamune; Keiichiro Fukumoto; Yumiko Yasunari; David Darwish

• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 289 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70213-9

✦ Synopsis

Previously (2) we described that diphenyltricyclo-[1.1.1.04'5 lpentanone underwent facile carbon-carbon bond cleavage reactions even under mild conditions. Its homolog, 8,6-diphenyltricyclo[2.1.1.05q6]hexan-2-one, however, has been found to be relatively stable and to react with carbonyl reagents to afford normal reaction products useful for further studies on this strained system. We wish to discuss reactions in which the carbene and carbonium ion could be produced at position 2 of the system. R2 3 Q I. R=O 4 II. R=N-NH-TS *. . XII. 'gH5 'sH5 R=H, NH2: The tosylhydrazone of ketone I was readily obtained in the usual manner, (II), m.p. 105-106°. A stirred