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-00000083.xml
Synlett 2011(3): 399-401
DOI: 10.1055/s-0030-1259327
DOI: 10.1055/s-0030-1259327
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Solid-State Structure of Some Substituted Hexahydro-1,4:5,8-diepoxynaphthalenes
Further Information
Received
18 November 2010
Publication Date:
19 January 2011 (online)
Publication History
Publication Date:
19 January 2011 (online)
![](https://www.thieme-connect.de/media/synlett/201103/lookinside/thumbnails/10.1055-s-0030-1259327-1.jpg)
Abstract
The structure of several carboxy-substituted hexahydro-1,4:5,8-diepoxynaphthalenes have been solved with X-ray crystallography, in some cases confirming previously contentious structures. The compounds of interest are constructed in efficient one-step 2 × [4+2] cycloaddition reactions from furan and acetylene carboxylate derivatives.
Key words
Diels-Alder reaction - cycloaddition - domino reaction - tandem reaction - furan
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Winkler JD.Kim HS.Kim S. Tetrahedron Lett. 1995, 34: 1900 -
1b
Nörret M.Sherburn MS. Angew. Chem. Int. Ed. 2001, 40: 4074 -
1c
Turner CI.Williamson RM.Turner P.Sherburn MS. Chem. Commun. 2003, 1610 -
2a
Cram DJ.Knox GR. J. Am. Chem. Soc. 1961, 83: 2204 -
2b
Cram DJ.Montgomery CS.Knox GR.
J. Am. Chem. Soc. 1966, 88: 515 -
2c
Paquette LA.Wyvratt MJ.Berk CH.Moerck RE. J. Am. Chem. Soc. 1978, 100: 5845 -
2d
Paquette LA.Balogh DW. J. Am. Chem. Soc. 1982, 104: 774 -
2e
Winkler JD. Chem. Rev. 1996, 96: 167 -
2f
Lautens M.Fillion E. J. Org. Chem. 1996, 61: 7994 -
2g
Lautens M.Fillion E. J. Org. Chem. 1997, 62: 4418 ; and references cited therein -
2h
Tietze LF.Brasche G.Gericke KM. Domino Reactions in Organic Synthesis 1st ed.: Wiley-VCH; Weinheim: 2006. p.280 - For the dimethyl ester, see:
-
3a
Gandhi RP.Chadha VK. Chem. Commun. 1968, 552 -
3b
Slee JD.LeGoff E.
J. Org. Chem. 1970, 35: 3897 -
3c
McCulloch AW.Smith DG.McInnes AG. Can. J. Chem. 1973, 51: 4125 ; see also ref. 5-8 - 4 For the dicyano derivative, see:
Weiss CD. J. Org. Chem. 1963, 28: 74 - 5
Diels O.Alder K. Ann. Chem. 1931, 490: 243 - 6
Diels O.Olsen S. J. Prakt. Chem. 1940, 156: 285 - 7
Woodward RB.Baer H. J. Am. Chem. Soc. 1948, 70: 1161 - 8
Stockman H. J. Org. Chem. 1961, 26: 2025 - 9
Kallos J.Deslongchamps P. Can. J. Chem. 1966, 44: 1239 -
12a
Sander M.Dehmlow EV. Org. Prep. Proced. Int. 2000, 32: 189 -
12b
Maier G.Jung WA. Tetrahedron. Lett. 1980, 21: 3875 -
13a
Gromov A.Enev V.Mulzer J. Synth. Commun. 2010, 40: 104 -
13b
Lasney M.-C.Ripoll J.-L. Bull. Soc. Chim. Fr. 1986, 5: 766 - For a related synthesis of the ethyl ester, see:
-
13c
McCulloch AW.Smith DG.McInnes AG. Can. J. Chem. 1974, 52: 1013 - 14
Sheldrick GM. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64: 112
References
For more detail, see the Supporting Information.
11See also ref. 5 and 9.