Photolysis of anthracene in a mixture consisting of 2% CF3SO3H in CF3CO2H (w/w), where anthracene is partially protonated, gives a mixture of oxidized, neutral and reduced monomeric and dimeric products, initiation of this chemistry being photoinduced electron transfer from anthracene to protonated anthracene.
References
1.
OlahG. A., Surya PrakashG. K., and SommerJ., Superacids, Wiley, New York, 1985.
2.
SmithG. P., DworkinA. S., PagniR. M., and ZinggS. P., J. Am. Chem. Soc., 1989, 111, 525.
3.
SmithG. P., DworkinA. S., PagniR. M., and ZinggS. P., J. Am. Chem. Soc., 1989, 111, 5075.
4.
CampbellJ. L. E., and JohnsonK. E., J. Am. Chem. Soc., 1995, 117, 7791.
5.
KingD., MantzR., and OsteryoungR., J. Am. Chem. Soc., 1996, 118, 11933.
6.
MaM., and JohnsonK. E., J. Am. Chem. Soc., 1995, 117, 1508.
7.
LeeC., WinstonT., UnniA., PagniR. M., and MamantovG., J. Am. Chem. Soc., 1996, 118, 4919.
8.
HondrogiannisG., LeeC. W., PagniR. M., and MamantovG., J. Am. Chem. Soc., 1993, 115, 9228.
9.
(a) CowanD. O., and DriskoR. L., Elements of Organic Photochemistry, Plenum, New York, 1976; (b) H.-D. Becker, Chem. Rev., 1993, 93, 145 and references cited therein.
10.
(a) MakorE. L., HofstraA., van der WaalsJ. H., Trans. Faraday Soc., 1958, 54, 66, 186; (b) D. M. Brouwer, E. L. Makor and C. MacLean, Carbonium Ions, ed. OlahG. A., SchleyerP. von R., Wiley-Interscience, New York, 1970, vol. II, ch. 20.
11.
NagaokaT., BerinstainA. B., GrillerD., and WaynerD. D. M., J. Org. Chem., 1990, 55, 3707.