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Electrophilic Substitution in Indoles. Part 13. The Synthesis and Rearrangement of 2-Deuteriospiro

DOI: 10.1039/P29870001221

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1221 - 1226 (1987)

Update date:2022-08-17

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Authors:

Ibaceta-Lizana, Juana S. L.Ibaceta-Lizana, Juana S. L.

Jackson, Anthony H.Jackson, Anthony H.

Prasitpan, NoojarePrasitpan, Noojare

Shannon, Patrick V. R.Shannon, Patrick V. R.

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Article abstract of DOI:10.1039/P29870001221

2-Deuterioindole was prepared from N-phenylsulphonylindole by lithiation, quenching with D2O, 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 deuteration of 2-deuterioindole) when treated in the same way, gave the indolyl oxobutanoic acid, 92 percent 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 which was 88 percent 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 kH/kD 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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Product name:1-phenylsulphonyl-<2-2H>indole

Cas No:114879-09-3

114879-09-3

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