Abstract
Treatment of 5-tert-butyl-8,12,14,16-tetramethyl[2.2]MCP with AlCl3-MeNO2 in benzene led to trans-tert-butylation to afford 8,12,14,16-tetramethyl[2.2]MCP in good yield along with tert-butylbenzene. On the other hand, the same treatment of 5-tert-butyl-8,12,14-trimethyl[2.2]MCP led to transannular cyclisation reaction and isomerisation reaction to afford the corresponding strainless 2-tert-butyl-3a,6,8-trimethyl-3,3a,4,5,9,10-hexahydropyrene in good yield.
References
1.
Kechn P.M.
, and
Rosenfield S. M.
(eds) Cyclophanes , Academic Press : New York , Vols 1 & 2 , 1983 .
2.
Vögtle F.
, Cyclophane-chemistry , Wiley , Chichester , 1993 .
3.
Ingraham L.L.
, J. Chem. Phys. , 1957 , 27 , 1228 .
4.
Allinger N.L.
,
Da Rooge M. A.
, and
Hermann R. B.
, J. Am. Chem. Soc. , 1961 , 83 , 1974 .
5.
Sato T.
,
Takemura T.
, and
Kainosho M.
, J. Chem. Soc., Chem. Commun. , 1974 , 97 .
6.
Sato T.
,
Matsui H.
, and
Komaki R.
, J. Chem. Soc., Perkin Trans. 1 , 1976 , 2053 .
7.
Takemura T.
, and
Sato T.
, Can. J. Chem. , 1976 , 54 , 3412 .
8.
Gleiter R.
, Tetrahedron Lett. , 1969 , 4453 .
9.
Cram D.J.
,
Allinger N. L.
, and
Steinberg H.
, J. Am. Chem. Soc. , 1954 , 76 , 6132 .
10.
Boschi R.
, and
Schmidt W.
, Angew. Chem., Int. Ed. Engl. , 1973 , 12 , 402 .
11.
Sato T.
, and
Takemura T.
, J. Chem. Soc., Perkin Trans. 2 , 1976 , 1195 .
12.
Tashiro M.
,
Yamato T.
,
Kobayashi K.
, and
Arimura T.
, J. Org. Chem. , 1987 , 52 , 3196 .
13.
Yamato T.
,
Maeda K.
,
Kamaimura H.
,
Noda K.
, and
Tashiro M.
, J. Chem. Res.(S) , 1995 , 310 ; (M) , 1995, 1865.
14.
Braun J.V.
, and
Neeles J.
, Ber. Dtsch. Chem. Ges. , 1934 , 67 , 1094 .
15.
Nauta W.TH.
, and
Dienske J. W.
, Rec. Trav. Chim. , 1936 , 55 , 1000 .
16.
Sato T.
,
Akabori S.
,
Muto S.
, and
Hata K.
, Tetrahedron , 1968 , 24 , 5557 .
17.
Sato T.
, and
Nishiyama K.
, J. Org. Chem. , 1972 , 37 , 3254 .
18.
Sato T.
, and
Takemura T.
, J. Chem. Soc., Perkin Trans. 2 , 1976 , 1195 .
19.
Tashiro M.
, and
Yamato T.
, Org. Prep. Proced. Int. , 1981 , 13 , 1 .
20.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1981 , 46 , 1543 .
21.
Tashiro M.
,
Koya K.
, and
Yamato T.
, J. Am. Chem. Soc. , 1982 , 104 , 3707 .
22.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1985 , 50 , 2939 .
23.
Yamato T.
,
Arimura T.
, and
Tashiro M.
, J. Chem. Soc., Perkin Trans. 1 , 1987 , 1 .
24.
Tashiro M.
,
Tsuge A.
,
Sawada T.
,
Makishima T.
,
Horie S.
,
Arimura T.
,
Mataka S.
, and
Yamato T.
, J. Org. Chem. , 1990 , 55 , 2404 .
25.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1983 , 48 , 1461 .
26.
Smith B.H.
, Bridged aromatic compounds , Academic Press , New York . 1964 .
27.
Vögtle F.
, and
Neumann P.
, Angew. Chem. , 1972 , 84 , 75 .
28.
Vögtle F.
, and
Neumann P.
, Angew. Chem. Int. Ed. Engl. , 1972 , 11 , 73 .
29.
Vögtle F.
, and
Neumann P.
, Synthesis , 1973 , 85 .
30.
Vögtle F.
, and
Höhner G.
, Top. Curr. Chem. , 1978 , 74 , 1 .
31.
Kechn P.M.
, and
Rosenfield S. M.
, Cyclophanes , Academic Press , New York . Vol. 1 , 1983 .
32.
Mitchell R.H.
, and
Boekelheide V.
, Tetrahedron Lett. , 1970 , 1197 .
33.
Mitchell R.H.
, and
Boekelheide V.
, J. Chem. Soc., Chem. Commun. , 1970 , 1555 .
34.
Anker W.
,
Bushnell G. W.
, and
Mitchell R. H.
, Can. J. Chem. , 1979 , 57 , 3080 .
35.
Mitchell R.H.
,
Carruther R. J.
,
Mazuch L.
, and
Dingle T. W.
, J. Am. Chem. Soc. , 1982 , 104 , 2544 .
36.
Mitchell R.H.
, and
Boekelheide V
, J. Am. Chem. Soc. , 1974 , 96 , 1547 .
37.
Hefelfinger D.T.
, and
Cram D. J.
, J. Am. Chem. Soc. , 1970 , 92 , 1073 .
38.
Hefelfinger D.T.
, and
Cram D. J.
, J. Am. Chem. Soc. , 1971 , 93 , 4767 .
39.
Cram D.J.
,
Helgeson D. L.
,
Lock D.
, and
Singer L. A.
, J. Am. Chem., Soc. , 1966 , 88 , 1324 .
