Some Diels-Alder adducts of 6-vinyl-1-oxa-4-thiaspiro[4.5]dec-6-ene

Parvez, M. ; Yadav, V. K. ; Senthil, G. (2001) Some Diels-Alder adducts of 6-vinyl-1-oxa-4-thiaspiro[4.5]dec-6-ene Acta Crystallographica Section C, 57 . pp. 82-85. ISSN 0108-2701

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Official URL: http://scripts.iucr.org/cgi-bin/paper?da1148

Related URL: http://dx.doi.org/10.1107/S0108270100013597

Abstract

6-Vinyl-1-oxa-4-thiaspiro[4.5]dec-6-ene has been reacted with dienophiles, such as N-phenylmaleimide (NPM), N-methyltriazoline-2,5-dione (MTAD) and dimethylacetylene dicarboxylate (DMAD), to assess the 1,3-diastereofacial selection caused by the acetal function. In each case, a mixture of two diastereoisomers was produced. The crystal structures of the products of the addition of NPM and MTAD syn to the acetal oxygen, 2-phenyl-2,3,3a,4,5,5a,6,7,8,9,9a,9b-dodecahydro-1H-benz[e] isoindole-6-spiro-2'-[1',3']oxathiolane-1,3-dione, C20H21NO3S, (IIa), and 2-methyl-5,7,8,9,10,10a-hexahydro-1H-1,2,4-triazolo[1,2-a] cinnoline-7-spiro-2'-[1',3']oxathiolane-1,3- dione, C13H17N3O3S, (IIIa), respectively, and the product of the addition of DMAD syn to the acetal sulfur, dimethyl 1,2,3,4,4a,7-hexahydronaphthalene-1-spiro-2'-[1',3']oxathiolane-5,6-dicarboxylate, C16H20O5S, (IVb), have been determined. All three structures are composed of independent molecules separated by normal van der Waals distances. The 1-oxa-4-thia heterocyclic ring has an envelope conformation in the three structures and the S-Csp3 bond distances differ significantly from each other, as observed in comparable structures; the remaining molecular dimensions are as expected.

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