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2-Deuterioindole was prepared from N-phenylsulphonylindole by lithiation, quenching with D, O, and hydrolysis. Treatment of the 2-deuterioindole Grignard reagent with succinic anhydride gave 4-(indol-3-yl) -4-oxobutanoic acid with partial loss of the deuterium from the 2-position. 2,3-Dideuterioindole (prepared by acid-catalysed deuteriation of 2-deuterioindole) when treated in the same way, gave the indolyl oxobutanoic acid, 92% deuteriated at the indolyl 2-position. Reduction to the deuterioindolylbutanol and treatment of its toluene-p-sulphonate with potassium t-butoxide give 2-deuterio-spiro[cyclopentane-3'-(3H)indolel which was 88% deuteriated at the 2-position. The kinetics of the acid-catalysed rearrangement of the deuterioindolenine and its non-deuteriated analogue were measured and the ratio k,/k, of the pseudo-first-order rate constants was found to be 1.08, showing that the isotope effect was very small.

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by this reagent. Kishner-Wolff reduction of (+)-isopinocamphone (IIIa; R = =O) gave a poor yield of pinanes consisting of 87% (g.1.c.) of the trans-isomer.