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Derivate des 5, 9-Methano-6, 7,8, 9-tetrahydro-5 H-benzocycloheptens und Umlagerungen zum 1, 4-Äthano-1,2,3,4-tetrahydronaphtalin-System

✍ Scribed by André P. Stoll; Hans-Rudolf Loosli; Peter Niklaus; Therese Zardin-Tartaglia

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
537 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

Derivatives of 5,9‐Methano,7,8,9‐tetrahydro‐5__H__‐benzocycloheptene and Rearrangements to the 1,4‐Ethano‐I,2,3,4‐tetrahydronaphthalene System

Reduction of the oxime 2 with Raney alloy gives the amine 3a, with AlH~3~ a mixture of the isomeric amines 3a and 3b, whilst LiAlH~4~ yields the aziridines 4a and 4b. The bicyclo[3.2.1]octane 4b rearranges under acidic conditions to the bicyclo[2.2.2]octane 5. The olefin 7 can be converted to the aminoalcohol 9 via the epoxide 8 and to the amine 13 using iodine isocyanate: the carbon skeleto. remains intact. However, treatment of the olefin 17 with iodine isocyanate leads to the bicyclo[2.2.2]octanes 21 and 24 in which a skeletal rearrangement has taken place. The configuration was determined by NMR. and X‐ray analysis.

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