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Regiocontrol in the cyclopropane ring cleavage of tricyclo$[^{1,3}]$decanes to hydrindane and decalin systems

Elsevier Science Ltd.
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  • Organic Chemistry


Lithium-liquid ammonia reduction of the cyclopropyl β-ketoester $2$ furnished a 1:1 mixture of hydrindane and decalin systems $3$ and $4$. Whereas under the same conditions the ketones $5$ and $6$ furnished the hydrindanones $10$ and $13$; and the hydroxy ester $7$ furnished the decalin system $14$, via the regiospecific cleavage of either $C_3--C_2$ bond or $C_3--C_1 $bond.

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