Reaction of dodecatrienylnickel with allene; formation of muscone

Abstract
The dodecatrienylnickel complex (1) absorbs 1 mol. equiv. of allene to yield the new bis-π-allyl intermediate (2); this absorbs a second mol. equiv. of allene to give eventually two isomeric dimethylene-cyclohexadecatrienes (4) and (5), or carbon monoxide to give the cyclic hydrocarbons (6) and (7) accompanied by the unsaturated ketone (8), which on hydrogenation forms (±)-muscone.

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