Abstract
The hydrolysis of 8-bromomethyl[2.2]metacyclophane 1a with a methoxy group at the 16-position was carried out in an 80% aqueous dioxane solution by refluxing in the presence of Nafion-H (a solid perfluorinated resin sulfonic acid) as a catalyst. The reaction yielded the corresponding 8-hydroxymethyl[2.2]metacyclophane 3 and the intramolecular C–C coupling product 2 with a spiro skeleton.
References
1.
(a)
Griffin R.W.
Jr.
. Chem. Rev. , 1963 , 63 , 45 .
2.
Smith B.H.
, Bridged Aromatic Compounds , Academic Press , New York , 1964 .
3.
Allinger N.L.
,
DaRooge M. A.
, and
Herman R. B.
, J. Am. Chem. Soc. , 1961 , 83 , 1974 .
4.
Sato T.
,
Wakabayashi M.
, and
Okamura Y.
, Bull. Chem. Soc. Jap , 1967 , 40 , 2363 .
5.
Sato T.
, and
Nishiyama K.
, J. Chem. Soc., Chem. Commun. , 1972 , 163 .
6.
Sato T.
, and
Nishiyama K.
, J. Org. Chem. , 1972 , 37 , 3254 .
7.
Sato T.
, and
Takemura T.
, J. Chem. Soc., Perkin Trans 2 , 1976 , 1195 .
8.
Tashiro M.
,
Yamato T.
,
Kobayashi K.
, and
Arimura T.
, J. Org. Chem. , 1987 , 52 , 3196 .
9.
Tashiro M.
, and
Yamato T.
, Chem. Lett. , 1982 , 61 .
10.
Olah G.A.
,
Iyer P. S.
, and
Prakash G. K.
, Synthesis , 1986 , 513 .
11.
(a)
Fukuzawa S.
,
Tsuchimoto T.
, and
Hiyama T.
, J. Org. Chem. , 1997 , 62 , 151 .
12.
Hanamoto T.
,
Sugimoto Y.
,
Sugino A.
, and
Inanaga J.
, Synlett , 1994 , 377 .
13.
Mine N.
,
Fujiwara Y.
, and
Taniguchi H.
, Chem. Lett. , 1986 , 357 .
14.
(a)
Yamato T.
,
Sakaue N.
,
Frusawa T.
,
Tashiro M.
,
Prakash G. K.
, and
Olah G. A.
, J. Chem Res. (S) , 1991 , 241 ; (M) 1991, 2414.
15.
Yamato T.
,
Hideshima C.
,
Prakash G. K.
, and
Olah G. A.
, J. Org. Chem. , 1991 , 56 , 2089 .
16.
Molandar G.A.
, Chem. Rev. , 1992 , 92 , 29 .
17.
(a)
Vitullo V.P.
,
Grabowski J.
, and
Sridharan S.
, J. Am. Chem. Soc. , 1980 , 102 , 6463 .
18.
Pross A.
, and
Shaik S.
, J. Am. Chem. Soc. , 1981 , 103 , 3702 .
19.
Tashiro M.
,
Arimura T.
, and
Yamato T.
, Chem. Pharm. Bull. , 1983 , 31 , 370 .