Facile Synthesis and Diels-Alder Reactions of 2,6-Divinyl-1,4-dithiin

Abstract

A new and facile synthetic pathway to 2,6-divinyl-1,4-dithiin, involving easily available precursors is reported. The utility of the title compound as a reactive diene in Diels-Alder reactions was demonstrated in the synthesis of various thianthrene derivatives.

Key words

alkynes - allenes - 2,6-divinyl-1,4-dithiin - Diels-Alder reactions - regioselectivity

References

• 1 Klar G. In Houben-Weyl (Methods of Organic Chemistry)   4th ed., Vol. E9a:  Thieme; Stuttgart: 1997.  p.250 
• 2 Andreu R. Garin J. Orduna J. Royo JM. Tetrahedron Lett.  2001,  42:  875 
• 3 Pluta K. Heterocycles  1999,  51:  2861 
• 4 Kobayashi K. Gajurel CL. Sulfur Rep.  1986,  7:  123 
• 5 Bryce MR. Chesney A. Lay AK. Batsanov AV. Howard JAK. J. Chem. Soc., Perkin Trans. 1  1996,  2451 
• 6 Remonen T. Hellberg J. Slatt J. Synth. Met.  1999,  101:  107 
• 7 Parham WE. Jones JD. J. Am. Chem. Soc.  1954,  76:  1068 
• 8 Parham WE. Stright PL. Hasek WR. J. Org. Chem.  1959,  24:  262 
• 9 Braverman S. Cherkinsky M. Birsa ML. Tichman S. Goldberg I. Tetrahedron Lett.  2001,  42:  7485 
• 10 Braverman S. Cherkinsky M. Birsa ML. Zafrani Y. Eur. J. Org. Chem.  2002,  3198 
• 11 Tolstikov GA. Tolstikov AG. Miftakhov MS. Spirikhin LV. Zh. Org. Khim.  1986,  22:  1620 ; Chem. Abstr. 1987, 107, 77466
• 12a Draber W. Chem. Ber.  1967,  100:  1559 
• 12b Gollnick K. Hartmann H. Tetrahedron Lett.  1982,  23:  2651 
• 12c Hayakawa K. Mibu N. Osawa E. Kanematsu K. J. Am. Chem. Soc.  1982,  104:  7136 
• 13 Schroth W. Billing F. Zschunke A. Z. Chem.  1969,  9:  184 
• 14 Stahly GP. Synth. Commun.  1987,  17:  1053 
• 15 Fringuelli F. Taticchi A. In Dienes in the Diels-Alder Reaction   Wiley; New York: 1990.  p.17