By John B. Pfeiffer

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P. 65 DCj12 mmHg, is obtained in ~ 80% yield. e. Hydroxyalkylation with oxirane. 2 g) of oxirane and 40 ml of THF is added dropwise at - 40 DC over 15 min to the solution of isobutenylpotassium, then the cooling bath is removed and the temperature allowed to rise to - 10 °C (note). The reaction mixture is hydrolysed with cold 3 to 4 N hydrochloric acid (a sufficient amount to bring the pH of the aqueous phase at ~ 5). The aqueous layer is extracted 6 times with small portions ofEt 20. The (unwashed) combined organic solutions are dried over MgS0 4 , after which the greater part ofthe solvent is distilled off at atmospheric pressure through a 40cm Vigreux column (bath temperature not higher than 110 DC).

H. Reaction with methyl isothiocyanate. 3 g) and 20 ml of THF is added over a few s to the suspension of allyllithium or isobutenyllithium and potassium bromide (method 1), which has been pre-cooled to - 90°C. The resulting reaction mixture (yellowish suspension) is stirred for an additional10min at - 60°C, then a mixture of20 g of 36 II Metallation of Aromatic and Olefinic Hydrocarbons 36% hydrochloric acid and 150 ml of water is added with vigorous stirring and without external cooling. The aqueous layer is extracted once with Et 2 0, after which the combined organic solutions are washed twice with water and subsequently dried over MgS0 4 .

This reaction, in which the 5-substituted derivative is converted into the thermodynamically more stable I-isomer, can be catalyzed by the alkali cyclopentadienylide. The easy isomerization is a consequence of the high acidity of the methine protons in the derivatives. ® It M'" - - ~ 2 ~ (( -+ E E 3 1E' Q 4 9 9 E and/

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