Citation: Hong Qi Li, Zhong Bao Zhang, Lin Li. New thiopyran-4-spiro-2'-(1,3-dithiolane):Formation mechanism and crystal structure[J]. Chinese Chemical Letters, ;2011, 22(3): 280-283. doi: 10.1016/j.cclet.2010.10.016 shu

New thiopyran-4-spiro-2'-(1,3-dithiolane):Formation mechanism and crystal structure

Key Laboratory of Science & Technology of Eco-Textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China

Received Date: 10 June 2010

Fund Project: Financial support of the project by Shanghai Municipal Natural Science Foundation (No. 06ZR14001) was acknowledged.

Ethylene trithiocarbonate reacted with dimethyl acetylenedicarboxylate to furnish tetramethyl thiopyran-4-spiro-2'-(l,3-dithiolane)-2,3,5,6-tetracarboxylate, a new thiopyran-4-spiro-2'-(l,3-dithiolane) heterocyclic compound, as the minor product together with the major product dimethyl 2-thioxo-l,3-dithiole-4,5-dicarboxylate. The new heterocycle was probably formed through a [2+2] cycloaddition between ethylene trithiocarbonate and dimethyl acetylenedicarboxylate followed by a 1,3-dipolar cycloaddition or [4+2] cycloaddition. Crystal structure of the new compound revealed that the thiopyran ring and 1,3-dithiolane moiety were perpendicular to each other.
- Tbiopyran-4-spiro-2'-(l,3-dithiolane),
- Cycloaddition,
- Mechanism,
- Crystal structure
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