Preparation of 1-Vinylcyclohexa-1,3-diene from 5,6-Diacetoxycyclooctene

✍ Scribed by Dr. W. Ziegenbein

• Publisher: John Wiley and Sons
• Year: 1965
• Tongue: English
• Weight: 227 KB
• Volume: 4
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.196500702

✦ Synopsis

blue-green needles, m.p. 64 OC; the trinitrobenzenr derivative of (5) melts at 139OC. Reduction of (3) also gives rise t o ( 5 ) . Further catalytic hydrogenation of ( 5 ) at normal pressure leads to an uptake of 4 moles of hydrogen, presumably to yield the hydrocarbon ( 6 ) , whose double bond can be detected with bromine or tetranitromethane. Although ( 4 ) is a cyclic conjugated system with 4n Tc-electrons (n = 4), it is surprisingly inert toward electrophilic reagents. It dissolves in 70 % perchloric acid and can be recovered unchanged from the solution by dilution at 0 "C.