A Convenient Synthesis of 2-Naphthylcyclopentanones and 2-Naphthylcyclohexanones from 1-Naphthylcycloalkenes

Maciej Góra; Michał K. Łuczyński; Janusz J. Sepioł

doi:10.1055/s-2005-865298

PAPER

A Convenient Synthesis of 2-Naphthylcyclopentanones and 2-Naphthylcyclohexanones from 1-Naphthylcycloalkenes

Maciej Góra*^a, Michał K. Łuczyński^b, Janusz J. Sepioł^a
^a Department of Organic Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland
Fax: +48(12)6340515; e-Mail: mgora@chemia.uj.edu.pl;
^b Department of Chemistry, University of Warmia and Mazury in Olsztyn, Plac Lodzki 4, 10-957 Olsztyn, Poland

Abstract

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Abstract

The oxidation of naphthylcycloalkenes with hydrogen peroxide or MCPBA followed by acid catalyzed rearrangement of diol (epoxide), afforded a series of naphthylcycloalkanones in a very simple manner. The conditions allow preparation of naphthylcycloalkanones on a multigram scale.

Key words

ketones - epoxidations - rearrangements - polycycles - alkenes

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References

1a Newman MS. Farbman MD. J. Am. Chem. Soc. 1944, 66: 1550

1b Ong HH. Anderson VB. J. Med. Chem. 1980, 23: 726

2a Mazzocchi PH. Kim CH. J. Med. Chem. 1982, 25: 1473

2b Klemm LH. Ziffer H. J. Org. Chem. 1956, 21: 274

2c McMurry JE. Beroldingen LA. Tetrahedron 1974, 30: 2027

3 Scamehorn RG. Hardacre JM. Lukanich JM. Sharpe LR. J. Org. Chem. 1984, 49: 4881

4 Umezawa B. Hoshino O. Sawaki S. Sato S. Numao N. J. Org. Chem. 1977, 42: 4272

5a Blazejewski JC. Cantacuzene D. Wakselman C. Tetrahedron 1973, 29: 4233

5b Ireland RE. Brown GG. J. Org. Chem. 1974, 39: 51

6a Barton DHR. Bhatnagar NY. Finet J.-P. Motherwell WB. Tetrahedron 1986, 42: 3111

6b Ooi T. Maruoka K. J. Am. Chem. Soc. 2003, 125: 10495

7a Alonso F. Yus M. Tetrahedron 1991, 47: 9119

7b Chen K. Koser GF. J. Org. Chem. 1991, 56: 5764

8a Wildman WC. J. Am. Chem. Soc. 1956, 78: 4181

8b Pecunioso A. Menicagli R. J. Org. Chem. 1989, 54: 2391

8c Ohwada T. Okabe K. Ohta T. Shudo K. Tetrahedron 1990, 46: 7539

8d Santos RP. Lopes RSC. Lopes CC. Synthesis 2001, 845

9 Kimura M. Kobayashi K. Yamamoto Y. Sawaki Y. Tetrahedron 1996, 52: 4303

10a House HO. Wasson RL. J. Am. Chem. Soc. 1957, 79: 1488

10b Caubere P. Guillaumet G. Moraud MS. Tetrahedron 1972, 28: 95

10c Thies RW. Shih H.-HJ. J. Org. Chem. 1977, 42: 280

11a Buchwald SL. Palucki M. J. Am. Chem. Soc. 1997, 119: 11108

11b Kawatsura M. Hartwig JF. J. Am. Chem. Soc. 1999, 121: 1473

11c Fox JM. Huang X. Chieffi A. Buchwald SL. J. Am. Chem. Soc. 2000, 122: 1360

11d Rutheford JL. Rainka MP. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 15168

12 Sepiol JJ. Gora M. Luczynski MK. Synlett 2001, 1383

13 Bailey AS. Dale GA. Shuttleworth AJ. Weizmann DP. J. Chem. Soc. 1964, 5110

14 Klemm LH. Hodes W. J. Am. Chem. Soc. 1951, 73: 5181

15 Bergmann F. Szmuszkowicz J. J. Am. Chem. Soc. 1947, 69: 1367

16 Szmuszkowicz J. Modest EJ. J. Am. Chem. Soc. 1950, 72: 571

17 Bergmann E. Bergmann F. J. Am. Chem. Soc. 1937, 59: 1443

18 Tinnemans AHA. Laarhoven WH. J. Chem. Soc., Perkin Trans. 2 1976, 1104

19 Kessar SV. Sobti AK. Joshi GS. J. Chem. Soc. C 1971, 259