A Novel Route to Geminal Dibromocyclobutanes: Syntheses of 2-Substituted Cyclobutanone Acetals and Their Reaction with Boron Tribromide

Journal of Organic Chemistry

Volumn 68, Issue 24, 2003, Pages 9394-9399

  Nordvik, Tore ^a   Brinker, Udo H ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

TRANSITION STATES;

BORON COMPOUNDS; HYDROLYSIS; SUBSTITUTION REACTIONS;

AROMATIC COMPOUNDS;

1 (1 PHENYLTHIOCYCLOPROPYL) 2 METHYL 1 PROPANOL; 1 (1 PHENYLTHIOCYCLOPROPYL) 2,2 DIMETHYL 1 PROPANOL; 1 (1 PHENYLTHIOCYCLOPROPYL) 3 METHYL 1 BUTANOL; 1 (1 PHENYLTHIOCYCLOPROPYL)CYCLOHEXYLMETHANOL; 1 (1 PHENYLTHIOCYCLOPROPYL)PHENYLMETHANOL; 1,1 DIMETHOXY 2 ISOBUTYLCYCLOBUTANE; 1,1 DIMETHOXY 2 ISOPROPYLCYCLOBUTANE; 1,1 DIMETHOXY 2 TERT BUTYLCYCLOBUTANE; 1,1 DIMETHOXYCYCLOBUTANE; 2 BENZYLCYCLOBUTANONE; 2 CYCLOBUTYLMETHYL 1,1 DIMETHOXYCYCLOBUTANE; 2 CYCLOBUTYLMETHYLCYCLOBUTANONE; 2 CYCLOHEXYL 1,1 DIMETHOXYCYCLOBUTANE; 2 CYCLOHEXYLCYCLOBUTANONE; 2 CYCLOHEXYLMETHYL 1,1 DIMETHOXYCYCLOBUTANE; 2 CYCLOHEXYLMETHYLCYCLOBUTANONE; 2 HEXYL 1,1 DIMETHOXYCYCLOBUTANE; 2 HEXYLCYCLOBUTANONE; 2 ISOBUTYLCYCLOBUTANONE; 2 ISOPROPYLCYCLOBUTANONE; 2 PHENYLCYCLOBUTANONE; 2 TERT BUTYLCYCLOBUTANONE; ACETAL DERIVATIVE; ALKYL GROUP; BORON DERIVATIVE; BROMINE DERIVATIVE; CYCLOBUTANE DERIVATIVE; CYCLOBUTANONE DERIVATIVE; PHENYL GROUP; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; SYNTHESIS;

EID: 0345254945     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035295o     Document Type: Article

References (33)

1. (a) Backes, J.; Brinker, U. H. Cyclopropylidene. In Houben-Weyl (Methoden der Organischen Chemie); Regitz, M., Ed.; Thieme: Stuttgart, 1989; Vol. E 19b, pp 391-510.
2. (b) Cyclobutylidene. In ref 1a, pp 511-541.
3. Brinker, U. H.; Boxberger, M. Angew. Chem., Int. Ed. Engl. 1984, 23, 974.
4. Brinker, U. H.; Weber, J. Tetrahedron Lett. 1986, 27, 5371.
5. Brinker, U. H.; Schrievers, T.; Xu, L. J. Am. Chem. Soc. 1990, 112, 8609.
6. (a) Kirmse W. In Carbene Chemistry, 2nd ed.; Academic: New York, 1971; pp 473-475.
7. (b) Baron, W. J.; DeCamp, M. R.; Hendrick, M. E.; Jones, M., Jr.; Levin, R. H.; Sohn, M. B. In Carbenes; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1973; Vol. 1, pp 42-44.
8. (a) Brown, R. F. C. Pyrolytic Methods in Organic Chemistry; Academic: New York, 1980.
9. (b) Brinker, U. H.; König, L. Chem. Ber. 1983, 116, 882.
10. (a) Willstätter, R.; Bruce, J. Ber. Dtsch. Chem. Ges. 1907, 40, 3979.
11. (b) Brinker, U. H.; Schenker, G. J. Chem. Soc., Chem. Commun. 1982, 679.
12. Blankenship, C.; Paquette, L. A. Synth. Commun. 1984, 14, 983.
13. CAS registry number provided by the author: 5445-51-2.
14. Salaun, J.; Hanack M. J. Org. Chem. 1975, 40, 1994.
15. Nordvik, T., Brinker, U. H. J. Org. Chem. 2003, 68, 7092.
16. Wittig, G.; Wilson, E. R. Chem. Ber. 1965, 98, 451.
17. Geluk, H. W. Synthesis 1970, 652.
18. Bartlett, P. D.; Ho, M. S. J. Am. Chem. Soc. 1974, 96, 627.
19. Schenker, G. MS Thesis, Ruhr Universität Bochum, Germany, 1982, p 13.
20. For a review, see: Fitjer, L. Cyclobutanes. Synthesis: By Ring Enlargement. In Houben-Weyl (Methods of Organic Chemistry); de Meijere, A., Ed. ; Thieme: Stuttgart, 1997; Vol. E 17e, pp 251-316.
21. Trost, B. M.; Keeley, D. E.; Arndt, H. C.; Rigby, J. H.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1977, 99, 3080.
22. Trost, B. M.; Keeley, D. E.; Arndt, H. C.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1977, 99, 3088.
23. Mino, T.; Masuda, S.; Nishio, M.; Yamashita, M. J. Org. Chem. 1997, 62, 2633.
24. For some examples comprising four-membered rings, see: (a) Clerici, A.; Pastori, N.; Porta, O. Tetrahedron 2001, 57, 217.
25. (b) Malatesta, V.; Jennings, M.; Hackett, P. Can. J. Chem. 1983, 61, 366,
26. (c) Tolstikov, G. A.; Miftakhov, M. F.; Akhmetvaleev, R. R.; Balezina, G. G.; Valeev, F. A. Zh. Org. Khim. 1990, 26, 2156.
27. (d) Guziec, F. S. Jr.; SanFilippo, L. J. J. Org. Chem. 1991, 56, 3178.
28. (e) Kirmse, W.; Olbricht, T. Synthesis 1975, 174.
29. Taylor, E. C.; Chiang, C.-S. Synthesis 1977, 467.
30. McOmie, J. F. W.; Watts, M. L.; West, D. E. Tetrahedron 1968, 24, 2289.
31. Youssefyeh, R. D.; Mazur, Y. Chem. Ind. (London) 1963, 609.
32. For an example, see: Brinker, U. H.; Ritzer, J. J. Am. Chem. Soc. 1981, 103, 2116.
33. Attempts to treat the cyclobutanone acetals with B-bromo-9-borabicyclo[3.3.1] nonane instead of boron tribromide led only to the corresponding cyclobutanones. For an example of ether cleavage with this reagent, see: Bhatt, M. V. J. Organomet. Chem. 1978, 156, 221.