Abstract
A convenient preparation of 8-benzyl[2.2]metaparacyclophanes using TiCl4 catalysed Friedel–Crafts benzylation of arenes with 8-bromomethyl[2.2]metaparacyclophane is described. The structures of these novel 8-benzyl[2.2]meta-paracyclophanes in solution are also discussed.
References
1.
Cram D.J.
,
Helgeson D.L.
,
Lock D.
, and
Singer L.A.
, J. Am. Chem. Soc. , 1966 , 88 , 1324 .
2.
Hefelfinger D.T.
, and
Cram D.J.
, J. Am. Chem. Soc. , 1971 , 93 , 4767 .
3.
Sherrod S.A.
, and
da Costa R.L.
, Tetrahedron Lett. , 1973 , 2083 .
4.
Boekelheide V.
,
Reingold I.D.
, and
Tuttle M.
, J. Chem. Soc., Chem. Commun. , 1973 , 406 .
5.
Mitchell R.H.
, and
Boekelheide V.
, J. Am. Chem. Soc. , 1974 , 96 , 1547 .
6.
Sherrod S.A.
,
da Costa R.L.
,
Barnes R.A.
, and
Boekelheide V.
, J. Am. Chem. Soc. , 1974 , 96 , 1565 .
7.
Mitchell R.H.
,
Otsubo T.
, and
Boekelheide V.
, Tetrahedron Lett. , 1975 , 219 .
8.
Vögtle F.
, Chem. Ber. , 1969 , 102 , 3077 .
9.
Neumann P.
, and
Vögtle F.
, Synthesis , 1973 , 85 .
10.
Hefelfinger D.T.
, and
Cram D.J.
, J. Am. Chem. Soc. , 1970 , 92 , 1073 .
11.
Hefelfinger D.T.
, and
Cram D.J.
, J. Am. Chem. Soc. , 1971 , 93 , 4767 .
12.
Akabori S.
,
Hayashi S.
,
Mawa M.
, and
Shiomi K.
, Tetrahedron Lett. , 1969 , 3727 .
13.
Renault A.
,
Cohen-Addad C.
,
Lajzerowicz-Bonneteau J.
,
Dutasta J.P.
, and
Cris M.J.
, Acta Crystallogr., Sect. B , 1987 , 43 , 480 .
14.
Yamato T.
,
Matsumoto J.
,
Tokuhisa K.
,
Tsuji K.
,
Suehiro K.
, and
Tashiro M.
, J. Chem. Soc., Perkin Trans. 1 , 1992 , 2675 .
15.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1981 , 46 , 1543 .
16.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1981 , 46 , 4556 .
17.
Tashiro M.
, and
Yamato T.
, J. Chem. Soc., Perkin Trans. 1 , 1984 , 2165 .
18.
Yamato T.
,
Matsumoto J.
,
Tokuhisa K.
,
Shigekuni M.
,
Suehiro K.
, and
Tashiro M.
, J. Org. Chem. , 1992 , 57 , 6969 .
19.
Yamato T.
,
Tokuhisa K.
, and
Tsuzuki H.
, Can. J. Chem. , 2000 , 78 , 238 .
20.
Yamato T.
,
Noda K.
, and
Tsuzuki H.
, New. J. Chem. , 2001 , 25 , 721 .
21.
Shimizu T.
,
Hita K.
,
Paudel A.
,
Tanaka J.
, and
Yamato T.
, J. Chem. Research , 2009 , 246 .
22.
Olah G.A.
, Acc. Chem. Res. , 1971 , 4 , 240 .
23.
Olah G.A.
,
Kobayashi S.
, and
Tashiro M.
, J. Am. Chem. Soc. , 1972 , 94 , 7448 .
24.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1983 , 48 , 1461 .
25.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1985 , 50 , 2939 .
26.
Smith B.H.
, in Bridged Aromatic Compounds , Academic Press , New York . 1964 .
27.
Vögtle F.
, and
Neumann P.
, Angew. Chem. , 1972 , 84 , 75 ; Angew. Chem. Int. Ed. Engl. , 1972, 11 , 73.
28.
Vögtle F.
, and
Neumann P.
, Synthesis , 1973 , 85 .
29.
Vögtle F.
, and
Höhner G.
, Top. Curr. Chem. , 1978 , 74 , 1 .
30.
Keehn P.M.
, and
Rosenfield S.M.
, Cyclophanes , Academic Press , New York . vol. 1 , 1983 .
31.
Tashiro M.
, and
Yamato T.
, J. Chem. Soc., Perkin Trans. 1 , 1979 , 176 .