Stereochemistry of seven-membered heterocycles: XLV. Highly diastereoselective addition of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate to 2-substituted 1,3-dithiacyclohept-5-enes

Author： Vafina R.   Gubaidullin A.   Kataeva O.   Litvinov I.   Shtyrlin Yu.   Klimovitskii E.  

Publisher： MAIK Nauka/Interperiodica

ISSN： 1070-4280

Source： Russian Journal of Organic Chemistry, Vol.42, Iss.10, 2006-10, pp. : 1563-1567

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Abstract

Conformationally heterogeneous 2-substituted 1,3-dithiacyclohept-5-enes (R = Ph, Me, t-Bu), which exist in solution as chair and boat conformers, react with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with high exo-diastereoselectivity: only the chair conformer is involved. The steric structure of 4-methyl-3,5-dithia-9,10-diazabicyclo[5.4.0]undeca-7,10-diene was determined by X-ray analysis. Its crystal packing and supramolecular structure were also analyzed.

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