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
<A NAME="RC02101SS-1">1</A>
Mizuno K.
Otsuji Y.
Top. Curr. Chem.
1994,
169:
304
<A NAME="RC02101SS-2">2</A>
Schuster DI.
Lem G.
Kaprinidis NA.
Chem. Rev.
1993,
93:
3
<A NAME="RC02101SS-3">3</A>
Muller F.
Mattay J.
Chem. Rev.
1993,
93:
99
<A NAME="RC02101SS-4">4</A>
Keukeleire D.
He S.
Chem. Rev.
1993,
93:
359
<A NAME="RC02101SS-5">5</A>
Cornelisse J.
Chem. Rev.
1993,
93:
615
<A NAME="RC02101SS-6">6</A>
McCullough JJ.
Chem. Rev.
1987,
87:
811
<A NAME="RC02101SS-7">7</A>
Gilbert A. In Synthetic Organic Photochemistry
Horspool WM.
Plenum Press;
New York:
1984.
p.1
<A NAME="RC02101SS-8">8</A>
Mattay J.
Tetrahedron
1985,
41:
2405
<A NAME="RC02101SS-9">9</A>
Caldwell RA.
Creed D.
Acc. Chem. Res.
1980,
13:
45
<A NAME="RC02101SS-10">10</A>
Mizuno, K.; Maeda, H.; Sugimoto, A.; Chiyonobu, K.; In Supramolecular Photochemistry; Ramamurthy V., Schanze K. S., Eds.; Marcel Dekker: in press.
<A NAME="RC02101SS-11A">11a</A>
McCullough JJ.
MacInnis WK.
Lock CJ.
Faggiani R.
J. Am. Chem. Soc.
1980,
102:
7780
<A NAME="RC02101SS-11B">11b</A>
McCullough JJ.
MacInnis WK.
Lock CJ.
Faggiani R.
J. Am. Chem. Soc.
1982,
104:
4644
<A NAME="RC02101SS-12">12</A>
Yokoyama A.
Mizuno K.
Org. Lett.
2000,
2:
3457
<A NAME="RC02101SS-13">13</A>
Mizuno K.
Nakanishi K.
Yasueda M.
Miyata H.
Otsuji Y.
Chem. Lett.
1991,
2001
<A NAME="RC02101SS-14">14</A>
Gilbert A.
Heath P.
Kashoulis-Koupparis A.
Ellis-Davies GCR.
Firth SM.
J. Chem. Soc., Perkin Trans. 1
1988,
31
<A NAME="RC02101SS-15">15</A>
Mizuno K.
Pac C.
Sakurai H.
J. Org. Chem.
1977,
20:
3313
<A NAME="RC02101SS-16">16</A>
Mizuno K.
Caldwell RA.
Tachibana A.
Otsuji Y.
Tetrahedron Lett.
1992,
33:
5779
<A NAME="RC02101SS-17">17</A>
Sakuragi H.
Tokumaru K.
Itoh H.
Terakawa K.
Kikuchi K.
Caldwell RA.
Hsu CC.
Bull. Chem. Soc. Jpn.
1990,
63:
1049
<A NAME="RC02101SS-18">18</A>
Mizuno K.
Pac C.
Sakurai H.
J. Am. Chem. Soc.
1974,
96:
2993
<A NAME="RC02101SS-19">19</A>
Caldwell RA.
Smith L.
J. Am. Chem. Soc.
1981,
103:
7263
<A NAME="RC02101SS-20">20</A>
Maeda H.
Waseda S.
Mizuno K.
Chem. Lett.
2000,
1238
<A NAME="RC02101SS-21">21</A>
Maeda H.
Sugimoto A.
Mizuno K.
Org. Lett.
2000,
2:
3305
<A NAME="RC02101SS-22">22</A>
Mizuno K.
Maeda H.
Inoue Y.
Sugimoto A.
Vo LP.
Caldwell RA.
Tetrahedron Lett.
2000,
41:
4913
<A NAME="RC02101SS-23">23</A>
Kimura M.
Nukada K.
Satake K.
Morosawa S.
Tamagake K.
J. Chem. Soc., Perkin Trans. 1
1984,
1431
<A NAME="RC02101SS-24">24</A>
Williams JLR.
Farid SY.
Doty JC.
Daly RC.
Specht DP.
Swarle R.
Borden DG.
Chang HJ.
Martic PA.
Pure Appl. Chem.
1977,
49:
523
<A NAME="RC02101SS-25A">25a</A>
Mizuno K.
Konishi S.
Takata T.
Inoue H.
Tetrahedron Lett.
1996,
37:
7775
<A NAME="RC02101SS-25B">25b</A>
Yoshimi Y.
Konishi S.
Maeda H.
Mizuno K.
Tetrahedron Lett.
2001,
42:
3475
<A NAME="RC02101SS-26">26</A>
Handbook of Chemistry and Physics
52nd ed:
West RC.
CRC Press;
Boca Raton, FL:
1972.
<A NAME="RC02101SS-27">27</A>
Reichhardt C.
Solvents and Solvent Effects in Organic Chemistry
2nd ed:
VCH;
Weinheim:
1988.
p.365
<A NAME="RC02101SS-28">28</A>
Mizuno K.
Pac C. In CRC Handbook of Organic Photochemistry and Photobiology
Horspool WM.
Song PS.
CRC Press;
Boca Raton, FL:
1994.
<A NAME="RC02101SS-29">29</A>
Pac C.
Pure Appl. Chem.
1986,
58:
1249
<A NAME="RC02101SS-30">30</A>
Handbook of Photochemistry
Murov SL.
Carmichael I.
Hug GL.
Marcel Dekker;
New York:
1993.
17.
p.76 and 85
<A NAME="RC02101SS-31">31</A>
Santamaria J. In Photoinduced Electron Transfer Part B
Fox MA.
Chanon M.
Elsevier;
Amsterdam:
1986.
p.483
<A NAME="RC02101SS-32">32</A>
Perrin DD.
Armarego WLF.
Purification of Laboratory Chemicals
3rd ed.:
Pergamon Press;
London:
1988.
