[4-CYCLOADDITIONS OF TETRACHLOROCYCLOP ROPENE TO 2-VINYLHETARENE AND 3-VINYLHETARENE - NOVEL [6+4]-CYCLODIMERIZATION AND [6+6]-CYCLODIMERIZATION AS FOLLOW-UP REACTIONS(2])

Authors
KEIL JM MASSA W RIEDEL R SEITZ G WOCADLO S
Citation
Jm. Keil et al., [4-CYCLOADDITIONS OF TETRACHLOROCYCLOP ROPENE TO 2-VINYLHETARENE AND 3-VINYLHETARENE - NOVEL [6+4]-CYCLODIMERIZATION AND [6+6]-CYCLODIMERIZATION AS FOLLOW-UP REACTIONS(2]), Tetrahedron letters, 35(43), 1994, pp. 7923-7926
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
43
Year of publication
1994
Pages
7923 - 7926
Database
ISI
SICI code
0040-4039(1994)35:43<7923:[OTRT2>2.0.ZU;2-U
Abstract
The reaction of 2-vinylpyrrole 1a with tetrachlorocyclopropene (2) aff ords the novel [6+4] cyclodimerisation product 13. In a similar fashio n the 3-vinylthiophenes 14 yield the [6+6] cyclodimerisation products 18. The intermediacy of the cyclic 2,3-dimethylene heteroaromatics 8 a nd 16 is assumed and a stepwise mechanism involving diradicals (such a s 12 and 19, resp.) is proposed.