Abstract
Irradiation of 2,3-dimethylbut-2-enyl 1-cyano-2-naphthylmethyl ether in the presence of Eu(hfc)3 in benzene site-selectively afforded the (2π + 2π) intramolecular photocycloadduct at the 1,2-position on the naphthalene ring. On the other hand, allyl 1-cyano-2-naphthylmethyl ether in the presence of Mg(ClO4)2 in acetonitrile gave the photocycloadduct at the 3,4-position as a sole product.
Key words
photochemistry - site-selectivity - cycloadditions - intramolecular photoadditions - cycloreversion
References
1
Mizuno K.
Otsuji Y.
Top. Curr. Chem.
1994,
169:
304
2
Schuster DI.
Lem G.
Kaprinidis NA.
Chem. Rev.
1993,
93:
3
3
Muller F.
Mattay J.
Chem. Rev.
1993,
93:
99
4
Keukeleire D.
He S.
Chem. Rev.
1993,
93:
359
5
Cornelisse J.
Chem. Rev.
1993,
93:
615
6
McCullough JJ.
Chem. Rev.
1987,
87:
811
7
Gilbert A. In Synthetic Organic Photochemistry
Horspool WM.
Plenum Press;
New York:
1984.
p.1
8
Mattay J.
Tetrahedron
1985,
41:
2405
9
Caldwell RA.
Creed D.
Acc. Chem. Res.
1980,
13:
45
10 Mizuno, K.; Maeda, H.; Sugimoto, A.; Chiyonobu, K.; In Supramolecular Photochemistry; Ramamurthy V., Schanze K. S., Eds.; Marcel Dekker: in press.
11a
McCullough JJ.
MacInnis WK.
Lock CJ.
Faggiani R.
J. Am. Chem. Soc.
1980,
102:
7780
11b
McCullough JJ.
MacInnis WK.
Lock CJ.
Faggiani R.
J. Am. Chem. Soc.
1982,
104:
4644
12
Yokoyama A.
Mizuno K.
Org. Lett.
2000,
2:
3457
13
Mizuno K.
Nakanishi K.
Yasueda M.
Miyata H.
Otsuji Y.
Chem. Lett.
1991,
2001
14
Gilbert A.
Heath P.
Kashoulis-Koupparis A.
Ellis-Davies GCR.
Firth SM.
J. Chem. Soc., Perkin Trans. 1
1988,
31
15
Mizuno K.
Pac C.
Sakurai H.
J. Org. Chem.
1977,
20:
3313
16
Mizuno K.
Caldwell RA.
Tachibana A.
Otsuji Y.
Tetrahedron Lett.
1992,
33:
5779
17
Sakuragi H.
Tokumaru K.
Itoh H.
Terakawa K.
Kikuchi K.
Caldwell RA.
Hsu CC.
Bull. Chem. Soc. Jpn.
1990,
63:
1049
18
Mizuno K.
Pac C.
Sakurai H.
J. Am. Chem. Soc.
1974,
96:
2993
19
Caldwell RA.
Smith L.
J. Am. Chem. Soc.
1981,
103:
7263
20
Maeda H.
Waseda S.
Mizuno K.
Chem. Lett.
2000,
1238
21
Maeda H.
Sugimoto A.
Mizuno K.
Org. Lett.
2000,
2:
3305
22
Mizuno K.
Maeda H.
Inoue Y.
Sugimoto A.
Vo LP.
Caldwell RA.
Tetrahedron Lett.
2000,
41:
4913
23
Kimura M.
Nukada K.
Satake K.
Morosawa S.
Tamagake K.
J. Chem. Soc., Perkin Trans. 1
1984,
1431
24
Williams JLR.
Farid SY.
Doty JC.
Daly RC.
Specht DP.
Swarle R.
Borden DG.
Chang HJ.
Martic PA.
Pure Appl. Chem.
1977,
49:
523
25a
Mizuno K.
Konishi S.
Takata T.
Inoue H.
Tetrahedron Lett.
1996,
37:
7775
25b
Yoshimi Y.
Konishi S.
Maeda H.
Mizuno K.
Tetrahedron Lett.
2001,
42:
3475
26
Handbook of Chemistry and Physics
52nd ed:
West RC.
CRC Press;
Boca Raton, FL:
1972.
27
Reichhardt C.
Solvents and Solvent Effects in Organic Chemistry
2nd ed:
VCH;
Weinheim:
1988.
p.365
28
Mizuno K.
Pac C. In CRC Handbook of Organic Photochemistry and Photobiology
Horspool WM.
Song PS.
CRC Press;
Boca Raton, FL:
1994.
29
Pac C.
Pure Appl. Chem.
1986,
58:
1249
30
Handbook of Photochemistry
Murov SL.
Carmichael I.
Hug GL.
Marcel Dekker;
New York:
1993.
17.
p.76 and 85
31
Santamaria J. In Photoinduced Electron Transfer Part B
Fox MA.
Chanon M.
Elsevier;
Amsterdam:
1986.
p.483
32
Perrin DD.
Armarego WLF.
Purification of Laboratory Chemicals
3rd ed.:
Pergamon Press;
London:
1988.