Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2003(6): 0849-0852
DOI: 10.1055/s-2003-38686
DOI: 10.1055/s-2003-38686
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York
Facile Synthesis and Diels-Alder Reactions of 2,6-Divinyl-1,4-dithiin
Further Information
Received
10 February 2003
Publication Date:
16 April 2003 (online)
Publication History
Publication Date:
16 April 2003 (online)
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
- 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