Strained Aromatic Systems. Synthesis of Cyclopropabenzocyclobutenes, Cyclopropanaphthocyclobutenes, and Related Compounds

Journal of Organic Chemistry

Volumn 45, Issue 21, 1980, Pages 4183-4193

  Davalian, Dariush ^a   Roller, Wolfgang ^a   Mansuri, Muzammil M ^a   Garratt, Peter J ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037544490     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo01309a024     Document Type: Article

References (38)

1. See: Callomon, J. H.; Dunn, T. M.; Mills, I. M. Philos. Trans. R. Soc. London, Ser. A. 1966, 259, 499.
2. Farthing, A. C. J. Chem. Soc. 1953, 3261. Brown, C. J. Philos. Trans. R. Soc. London, Ser. A.1953, 3265. Cram, D. J.; Steinberg, H. J. Am. Chem. Soc. 1951, 73, 5691.
3. See: Hubert, A. J. J. Chem. Soc. C 1967, 13; Longone, D. T.; Chow, H. S. J. Am. Chem. Soc. 1970, 92, 994; Misumi, S.; Otsubo, T. Acc. Chem. Res. 1978, 11, 251.
4. Cram, D. J.; Cram, J. M. Acc. Chem. Res. 1971, 4, 204.
5. See: van Tamelen, E. E.; Pappas, S. P. J. Am. Chem. Soc. 1962, 84, 3789; Burgstahler, A. W.; Chien, P.-L.; Abdel-Rahman, M. O. Acc. Chem. Res.1964, 86, 5281.
6. Lothrop, W. C. J. Am. Chem. Soc. 1941, 63, 1187.
7. Cava, M. P.; Napier, D. R. J. Am. Chem. Soc. 1956, 78, 500.
8. Cava, M. P.; Deana, A. A.; Muth, K. J. Am. Chem. Soc. 1960, 82, 2524.
9. Cava, M. P.; Shirley, R. L. J. Am. Chem. Soc. 1960, 82, 654. Cava, M. P.; Shirley, R. L.; Erickson, B. W. J. Org. Chem. 1962, 27, 755.
10. Anet, R.; Anet, F. A. L. J. Am. Chem. Soc. 1964, 86, 525.
11. Vogel, E.; Grimme, W.; Korte, S. Tetrahedron Lett. 1965, 3625.
12. See: Halton, B. Chem. Rev. 1973, 73, 113; Billups, W. E. Acc. Chem. Res. 1978, 11, 245.
13. For preliminary accounts of parts of this work, see: Davalian, D.; Garratt, P. J. J. Am. Chem. Soc. 1975, 97, 6883; Tetrahedron Lett. 1976, 2815; Davalian, D.; Garratt, P. J.; Mansuri, M. M. J. Am. Chem. Soc. 1978, 100, 980.
14. However, see: Saward, C. J.; Vollhardt, K. P. C. Tetrahedron Lett. 1975, 4539.
15. Billups, W. E.; Blakeney, A. J.; Chow, W. Y. J. Chem. Soc. D 1971, 1461.
16. Garrett, J. M.; Fonken, G. J. Tetrahedron Lett. 1969, 191.
17. Cope, A. C.; Herrick, E. Org. Synth. 1950, 30, 29.
18. Makosza, M.; Wawrzyniewicz, M. Tetrahedron Lett. 1969, 4659.
19. Muskat, I. E.; Becker, B. C.; Lowenstein, J. S. J. Am. Chem. Soc. 1930, 52, 326.
20. Gloss, G. L.; Boll, W. A. J. Am. Chem. Soc. 1963, 85, 3904.
21. Banwell, M. G.; Blattner, R.; Browne, A. R.; Craig, J. T.; Halton, B. J. Chem. Soc., Perkin Trans. 1 1977, 2165.
22. See: Huisgen, R.; Boche, G.; Hecht, W.; Huber, H. Angew. Chem., Int. Ed. Engl. 1966, 5, 585.
23. Alder, K.; Dortmann, H. A. Chem. Ber. 1954, 87, 1492.
24. Thummel, R. P. J. Am. Chem. Soc. 1976, 98, 628.
25. Thummel, R. P.; Nutakul, W. J. Org. Chem. 1977, 42, 300.
26. Hexamethylbenzene has a maximum at 278 nm: Stern, E. S.; Timmons, C. J. “Electronic Absorption Spectroscopy in Organic Chemistry”, 3rd ed.; Arnold: London, 1970. Cyclophanes have bands at longer wavelength; cf. ref 3.
27. Günther, H.; Jikeli, G.; Schmickler, H.; Prestien, J. Angew. Chem., Int. Ed. Engl. 1973, 12, 762.
28. Bee, L. K.; Garratt, P. J.; Mansuri, M. M. J. Am. Chem. Soc., in press.
29. Heine, H.-G. Chem. Ber. 1971, 104, 2869.
30. Dehmlow, E. V. Chem. Ber. 1967, 100, 3260.
31. Cookson, R. C.; Giliani, S. S. H.; Stevens, I. D. R. Tetrahedron Lett. 1962, 615.
32. Thummel, R. P.; Nutakul, W. J. Am. Chem. Soc. 1978,100, 6171.
33. Tanimoto, S.; Schafer, R.; Ippen, J.; Vogel, E. Angew. Chem., let. Ed. Engl. 1976, 15, 613.
34. Breslow, R.; Ryan, G.; Groves, J. T. J. Am. Chem. Soc. 1970, 92, 988.
35. Smith, W. B.; Shoulders, B. A. J. Phys. Chem. 1965, 69, 2022.
36. See: Crossland, R. K.; Servís, K. L. J. Org. Chem. 1970, 35, 3195.
37. Wittig, G.; Haag, W. Chem. Ber. 1955. 88, 1654.
38. Martin, E. L. J. Am. Chem. Soc. 1936, 58, 1438.