Cis-Decahydronaphthalene

All reactions were performed at room temperature with 3 mmol of cyclohexeneoxide, 3 mmol of cis decahydronaphthalene (internal standard), unsupported catalyst (homo) or 100 mg of heterogeneous complex and 3.15 mmol TMSN3 in 1 ml of dry Et20. 

Naphthalene is reduced to 1,4-dihydronaphthalene by sodium and alcohol. Isomerization of this product to 3,4-dihydronaphthalene occurs with sodamide in liquid ammonia. Tetrahydronaphthalene (tetralin) is formed from naphthalene by sodium in amyl alcohol or by reduction with nickel-aluminum alloy and aqueous alkali. Catalytic hydrogenation of naphthalene can be stopped at the tetralin stage over copper chromite, Raney nickel, or alkali metal catalysts. cis-Decahydronaphthalene is produced by high-pressure hydrogenation of tetralin over Adams catalyst, whereas a mixture of cis- and trans-decalins is obtained from naphthalene under the same conditions. ... 

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