A Novel Approach to the Rare 4- and 5-Alkylindan-2-ols

Abstract

The rare 4- and 5-alkylindan-2-ols have been synthesized in 62–72% yields by formal 1,6- and 1,4-nucleophilic ring opening of the 2-hydroxyindan 3a,7a-oxide, respectively.

References

1. Y. Nakada, S. Muramatsu, M. Asai, S. Ohno and Y. Yura, Agric. Biol. Chem., 1978, 42, 1357.
2. N. Inamoto, S. Masuda, K. Tori, K. Aono and H. Tanida, Can. J. Chem., 1967, 45, 1185.
3. W. H. Rastetter, M. D. Lewis, T. J. Richard and J. Adams, J. Org. Chem., 1979, 44, 3175.
4. P. Radlick and W. Rosen, J. Am. Chem. Soc., 1966, 88, 3461 ; for a review, see R. G. Harvey, Synthesis, 1970, 161.
5. G. J. Kasperek, P. Y. Bruice, T. C. Bruice, H. Yagi and D. M. Jerina, J. Am. Chem. Soc., 1973, 95, 6041.
6. T. Imamoto, T. Kusumoto, Y. Tawarayama, Y. Sugiura, T. Mita, Y. Hatanaka and M. Yokoyama, J. Org. Chem., 1984, 49, 3904.