Abstract
McMurry cyclisation of 1,4-bis(3-acetyl-4-methoxyphenyl)butane afforded flexible 4,16-dimethoxy-1,2-dimethyl[2.4] metacyclophan-1-ene, which was converted to the corresponding triple bridged 8,17-dimethoxy-1,2-dimethyl-10-thia[2.3.4](1,3,5)cyclophan-1-ene. The conformational studies of these cyclophan-1-enes in solution are also described.
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References
1.
Pelligrin M.
, Recl. Trav. Chim. Pays-Bas Belg. , 1899 , 18 , 458 .
2.
Mitchell R.H.
,
Vinod T.K.
, and
Bushnell G.W.
, J. Am. Chem. Soc. , 1985 , 107 , 3340 .
3.
Fujise Y.
,
Nakasato Y.
, and
Itô S.
, Tetrahedron Lett. , 1986 , 27 , 2907 .
4.
Mitchell R.H.
, and
Boekelheide V.
, J. Am. Chem. Soc. , 1974 , 96 , 1547 .
5.
Staab H.A.
,
Riebel W.R.K.
, and
Krieger C.
, Chem. Ber. , 1985 , 118 , 1230 .
6.
Boekelheide V.
, and
Hollins R.A.
, J. Am. Chem. Soc. , 1970 , 92 , 3512 .
7.
Sekine Y.
, and
Boeckelheide V.
, J. Am. Chem. Soc. , 1981 , 103 , 1777 .
8.
Bodwell G.J.
,
Bridson J.N.
,
Cyrañski M.K.
,
Kennedy J.W.J.
,
Krygowski T.M.
,
Mannion M.R.
, and
Moller D.O.
, J. Org. Chem. , 2003 , 68 , 2089 .
9.
Yamato T.
,
Fujita K.
,
Futatsuki K.
, and
Tsuzuki H.
, Can. J. Chem. , 2000 , 78 , 1089 .
10.
Yamato T.
,
Miyamoto S.
,
Hironaka T.
, and
Miura Y.
, Org. Lett. , 2005 , 7 , 3 .
11.
Yamato T.
,
Fujita K.
, and
Tsuzuki H.
, J. Chem. Soc. Perkin Trans. 1 , 2001 , 2089 ,
12.
McMurry J.E.
, Chem. Rev. , 1989 , 89 , 1513 .
13.
Grützmacher H.-F.
, and
Neumann E.
, Chem. Ber. , 1993 , 126 , 1495 .
14.
Yamato T.
,
Fujita K.
,
Okuyama K.
, and
Tsuzuki H.
, New. J. Chem. , 2000 , 221 .
15.
Yamato T.
,
Fujita K.
,
Abe T.
, and
Tsuzuki H.
, New J. Chem. , 2001 , 25 , 728 .
16.
Yamato T.
,
Matsumoto J.
,
Sato M.
,
Noda K.
, and
Tashiro M.
, J. Chem., Soc., Perkin Trans. 1 , 1995 , 1299 .
17.
Yamato T.
,
Matsumoto J.
, and
Fujita K.
, J. Chem., Soc., Perkin Trans. 1 , 1998 , 123 .
18.
Keehn P.M.
, and
Rosenfield S.M.
(eds), Cyclophanes Academic Press , New York , 1983 , vol. 1 , chap. 6, p. 428 .
19.
Vögtle F.
, Cyclophane-chemistry , Wiley , Chichester , 1993 .
20.
Krois D.
, and
Lehner H.
, Tetrahedron , 1982 , 38 , 3319 .
21.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1981 , 46 , 4556 .
22.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1983 , 48 , 1461 .
23.
Saisyo T.
,
Shiino M.
,
Shimizu T.
,
Paudel A.
, and
Yamato T.
, J. Chem. Res. , 2008 , 479 .
24.
Bodwell G.J.
,
Houghton T.J.
,
Koury H.E.
, and
Yarlagadda B.
, Synlett , 1995 , 751 .
25.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1981 , 46 , 1543 .
26.
Tashiro M.
,
Koya K.
, and
Yamato T.
, J. Am. Chem. Soc. , 1982 , 104 , 3707 .
27.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1985 , 50 , 2939 .
28.
Yamato T.
,
Arimura T.
, and
Tashiro M.
, J. Chem. Soc., Perkin Trans. 1 , 1987 , 1 .
29.VARIAN NMR Spectra Catalogue , Varian Associates, 1962 and 1963 , spectra No. 625 and 626.
30.
Oki M.
, Applications of dynamic NMR spectroscopy to organic chemistry; VCH : Deerfield Beach, FL 1985 .
