Acta Crystallographica Section C

Crystal Structure Communications

Volume 59, Part 5 (May 2003)

organic compounds

gg1163 scheme

Acta Cryst. (2003). C59, o250-o253 [ doi:10.1107/S0108270103006504 ]

1,3-Thiazolidine derivatives from regioselective [2+3]-cycloadditions of azomethine ylides with thioketones

M. Domagala, A. Linden, T. A. Olszak, G. Mloston and H. Heimgartner

Abstract: The title compounds, namely dimethyl (2RS)-2,3-diphenyl-1,3-thiazolidine-5-spiro-2'-adamantane-4,4-dicarboxylate methanol solvate, C₂₈H₃₁NO₄S·0.275CH₄O, and dimethyl (4RS)-3,4-diphenyl-1,3-thiazolidine-5-spiro-9'-(9'H-fluorene)-2,2-dicarboxylate, C₃₁H₂₅NO₄S, were obtained from dipolar [2+3]-cycloadditions of an azomethine ylide with adamantanethione and thiofluorenone, respectively. The structures show that the choice of thioketone affects the regioselectivity of the cycloaddition. The asymmetric unit of the former structure contains two molecules of the thiazolidine derivative plus a site for a partial occupancy (55%) methanol molecule. O-HO and C-HO interactions link two of each of these entities into closed centrosymmetric hexamers. The five-membered ring in each structure has an envelope conformation.

Formula: C₂₈H₃₁NO₄S·0.275CH₄O and C₃₁H₂₅NO₄S


	Structure factor file (CIF format) (548.7 kbytes) Contains datablock VI

	Structure factor file (CIF format) (463.3 kbytes) Contains datablock VII

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