(+-)-alpha-Pinene → Tetramethyl para-menthane-2,6-diyldiphosphonate

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In a manner similar to the previous examples, 233 ml of dimethyl hydrogen phosphite was stirred with 4.6 ml of di-tertiary-butyl peroxide at 140°-150° while α-pinene (81 ml) was added over a period of 15 minutes. After maintaining the reaction mixture at 140° for 18 hours, an additional 4.6 ml of di-tertiary-butyl peroxide was added. After heating an additional 30 minutes, the reaction mixture was subjected to distillation which provided the di-adduct. The NMR spectrum showed the methyl ester groups as a multiplet consisting mainly of 2 spikes at 3.70δ and 3.88δ along with the remainder of the protons between 0.7δ and 3.5δ.

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