Cleavage of carboxylic esters effected by organotin oxides and hydroxides under classical heating and microwave irradiation. A comparative study

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5229-5232

  Furlán, Ricardo L E ^a   Mata, Ernesto G ^a   Mascaretti, Oreste A ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE;

ARTICLE; CATALYSIS; HYDROLYSIS; MICROWAVE RADIATION; REACTION ANALYSIS;

EID: 0030598046     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01071-4     Document Type: Article

References (26)

1. 1. For a recent review, see: Jarowicki, K.; Kocienski, P. J. Contemporary Organic Synthesis 1995, 2, 316 and references cited therein.
2. 2. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. J. Org. Chem. 1994, 59, 7259.
3. 3. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. J. Chem. Soc., Perkin Trans 1 1996, 995.
4. 4. The chemistry of organotin oxide and hydroxides has been reviewed rather extensively, see: a) Bloodworth A. J.; Davies, A. G. In Organotin Compounds; Sawyer, A. Ed.; vol 1; M. Dekker: New York, 1971, pp. 158-252.
5. b) Davies, A. G.; Smith, P. G. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W. Eds.; vol. 2; Pergamon Press: Oxford, 1982, pp. 519-627.
6. c) Davies, A. G. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Eds.; vol. 2; Elsevier: Oxford, 1995, pp. 217-303.
7. d) Pereyre, M.; Quintard, J.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987.
8. e) Omae, I. Organotin Chemistry; Elsevier: New York. 1989.
9. f) Harrison, P. G. Chemistry of Tin, Blackie: Glasgow 1989.
10. 5. In solution, triphenyltin hydroxide is in equilibrium with bis(triphenyltin) oxide and water. See 4a, p. 195.
11. 6. See path b on the mechanism II of reference 2. One of the referees pointed out this alternative path for mechanism II. Now, we can rule out this possibility.
12. 3SnOH, incorrectly assigned by Reichle, W. T. Inorg. Chem. 1966, 5, 87, was effectively carried out with bis(trineophyltin) oxide. For the correct structure and physical and spectroscopic properties see: Zimmer, H; Homberg, O. A.; Jayawant, M. J. Org. Chem. 1966, 31, 3857. We now suggest that the lack of reactivity of bis(trineophyltin) oxide should be attributed to the steric restriction of the very bulky neophyl groups.
13. 3SnOH, incorrectly assigned by Reichle, W. T. Inorg. Chem. 1966, 5, 87, was effectively carried out with bis(trineophyltin) oxide. For the correct structure and physical and spectroscopic properties see: Zimmer, H; Homberg, O. A.; Jayawant, M. J. Org. Chem. 1966, 31, 3857. We now suggest that the lack of reactivity of bis(trineophyltin) oxide should be attributed to the steric restriction of the very bulky neophyl groups.
14. 3SnOH, incorrectly assigned by Reichle, W. T. Inorg. Chem. 1966, 5, 87, was effectively carried out with bis(trineophyltin) oxide. For the correct structure and physical and spectroscopic properties see: Zimmer, H; Homberg, O. A.; Jayawant, M. J. Org. Chem. 1966, 31, 3857. We now suggest that the lack of reactivity of bis(trineophyltin) oxide should be attributed to the steric restriction of the very bulky neophyl groups.
15. 8. For Lewis acidities estimation by using the phosphine oxide IR frequency shift method, see: a) Vedejs, E.; Erdman, D. E.; Powell, D. R. J. Org. Chem. 1993, 55, 6162.
16. b) Frazer, M. J.; Gerrard, W.; Patel, J. K. J. Chem. Soc. 1960, 726.
17. 9. For recent reviews on theoretical concepts, equipment design and applications of microwave energy in organic chemistry, see: a) Strauss, C, R.; Trainor, R. W. Aust. J. Chem. 1995, 48, 1665.
18. b) Caddick, S. Tetrahedron 1995, 38, 10403.
19. c) Abramovich, R. A. Org. Prep. Proced. Int. 1991, 23, 683.
20. d) Mingos, D. M. P.; Baghurst, D. R. Chem. Soc. Rev. 1991, 20, 1.
21. 10. Varma, R. S.; Chatterjee, A. K.; Varma, M. Tetrahedron Lett. 1993, 34, 4603.
22. 11. Varma, R. S.; Varma, M.; Chatterjee, A. K. J. Chem. Soc., Perkin Trans 1 1993, 999.
23. 12. Ley, S. V.; Mynett, D. M. Synlett 1993, 793.
24. 13. Bose, A. K.; Manhas, M. S.; Ghosh, M.; Shah, M.; Raju, V. S.; Bari, S. S.; Newaz, S. N.; Banik, B. K.; Chaudhary, A. G.; Bakarat, K. J. J. Org. Chem. 1991, 56, 6968.
25. 14. Despite the convenience of the MORE technique we use toluene which is a solvent with a low dielectric constant and fairly transparent to microwave irradiation because we have made an extensive use of this solvent for the cleavage of carboxylic esters by BBTO under conventional heating. See, references 2 and 3.
26. 15. Reactions were conducted in a commercial microwave oven without any modification. The approximate temperature was 103°C. Measurements of temperatures induced by microwave heating by using a commercial microwave oven are not exact. For a procedure of measurement, see reference 13.