Abstract
Acylation of 5,13-di-tert-butyl-8,16-dimethyl[2.2]metacyclophane with acid anhydrides led to mono-ipso-acylation at the tert-butyl group to give 5-acyl-13-tert-butyl-8,16-dimethyl[2.2]metacyclophanes, from which the second electrophilic substitition with acid anhydrides can be strongly suppressed because of deactivation of the second aromatic ring by acyl group introduced by the through-space electronic interaction.
References
1.
Medium-sized Cyclophanes. part 82:
Shimizu T.
,
Hita K.
,
Paudel A.
,
Tanaka J.
, and
Yamato T.
, J. Chem. Res. , 2009 , 246 .
2.
Griffin R.W.
Jr.
., Chem. Rev. , 1963 , 63 , 45 .
3.
Cram D.J.
, Acc. Chem. Res. , 1971 , 4 , 204 .
4.
Brown C.J.
, J. Chem. Soc. , 1953 , 3278 .
5.
Keehn P.M.
, and
Rosenfield S. M.
(eds), Cyclophanes , Academic Press , New York , 1983 , Vol. 1 , Chap. 6, p. 428 .
6.
Tashiro M.
,
Yamato T.
, and
Kobayashi K.
, J. Org. Chem. , 1984 , 49 , 3380 .
7.
Yamato T.
,
Matsumoto J.
,
Ando T.
,
Tokuhisa K.
, and
Tashiro M.
, J. Chem. Res. , 1991 , (S) 276 .
8.
Yamato T.
,
Kamimura H.
, and
Furukawa T.
, J. Org. Chem. , 1997 , 62 , 7560 .
9.
Moodie R.B.
, and
Schofield K.
, Acc. Chem. Res. , 1976 , 9 , 297 .
10.
Fischer A.
, and
Röderer R.
, Can. J. Chem. , 1976 , 54 , 3978 .
11.
Fischer A.
, and
Teo K. C.
, Can. J. Chem. , 1978 , 56 , 258 .
12.
Fischer A.
, and
Teo K. C.
, Can. J. Chem. , 1978 , 56 , 1758 .
13.
Suzuki H.
, Synthesis , 1977 , 217 .
14.
Myhre PC
., and
Beug M.
, J. Am. Chem. Soc. , 1966 , 88 , 1568 .
15.
Myhre PC
., and
Beug M.
, and
James L. L.
, J. Am. Chem. Soc. , 1968 , 90 , 2105 .
16.
Myhre PC
.,
Beug M.
,
Brown K. S.
, and
Östman B.
, J. Am. Chem. Soc. , 1971 , 93 , 3452 .
17.
Verboom W.
,
Durie A.
,
Egberink R. J.
,
Asfari M. Z.
, and
Reinhoudt D. N.
, J. Org. Chem. , 1992 , 57 , 1313 .
18.
Yamato T.
,
Kamimura H.
,
Noda K.
, and
Tashiro M.
, J. Chem. Res. (S) , 1994 , 424 , (M) 2401.
19.
Tashiro M.
, and
Yamato T.
, J. Org. Chem. , 1981 , 46 , 1543 .
20.
Tashiro M.
, and
Yamato T.
, J. Am. Chem. Soc. , 1982 , 104 , 3701 .
21.
Tashiro M.
, and
Yamato T.
, J. Chem. Soc., Perkin Trans. 1 , 1979 , 176 .
22.
Cacace F.
,
Crestoni M. E.
,
Fornarini S.
, and
Kuck D.
, J. Am. Chem. Soc. , 1993 , 115 , 1024 .
23.
Yamato T.
,
Matsumoto J.
,
Kabu S.
,
Takezaki Y.
, and
Tashiro M.
, J. Chem. Res. (S) 1993 , 44 .
24.
Yamato T.
,
Maeda K.
,
Kamimura H.
,
Noda K.
, and
Tashiro M.
, J. Chem. Res. (S) , 1995 , 310 ; (M) 1865.
