The gas-phase Meerwein reaction

Chemistry - A European Journal

Volumn 6, Issue 5, 2000, Pages 897-905

  Moraes, Luiz Alberto B ^a   Eberlin, Marcos N ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Acylium ions; Epoxides; Ion molecule reactions; Mass spectrometry; Thioacylium ions; Thioepoxides

Indexed keywords

EPOXIDE;

ACUTE PHASE RESPONSE; ACYLATION; ARTICLE; GAS TRANSPORT; ISOMERISM; PHASE TRANSITION; PROTON TRANSPORT; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034599120     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000303)6:5<897::aid-chem897>3.0.co;2-h     Document Type: Article

References (47)

1. a) B. Rickborn in Comprehensive Organic Synthesis, Vol. 3 (Eds.; B. M. Trost, I. Fleming), Pergamon Press, New York, 1991;
2. b) F. A. Carey, R. J. Sundberg Advanced Organic Chemistry, 1983, Plenum Press, New York.
3. K. L. Williamson, W. S. Johnson, J. Org. Chem. 1961, 26, 4563.
4. a) W. V. MacConnell, W. H. Moore, J. Org. Chem. 1965, 28, 822;
5. b) B. Bardili, H. Marchall-Weyerstahl, P. Weyerstahl, Justus Liebigs Ann. Chem. 1985, 275.
6. a) M. T. Bogert, R. O. Roblin, Jr., J. Am. Chem. Soc. 1933, 55, 3741;
7. b) T. Bersin, G. Willfang, Chem. Ber. 1937, 70, 2167;
8. c) H. C. van der Plas, Ring Transformations of Heterocycles. Vol. 1, 1973, Academic Press, New York.
9. H. Meerwein, Chem. Ber. 1955, 67, 374.
10. G. A. Olah, A. Gramain, A. M. White in Carbonium Ions, Vol. 5 (Eds.: G. A. Olah, P. von R. Schleyer), Wiley Interscience, New York, 1976.
11. a) D. A. Chatfield; M. M. Bursey, J. Am. Chem. Soc. 1976, 98, 6492;
12. b) R. H. Staley, R. D. Wieting, J. L. Beauchamp, J. Am. Chem. Soc. 1977, 99, 5964;
13. c) M. Kumakura, T. Sigiura J. Phys. Chem. 1978, 82, 639;
14. d) C. Sparapani, M. Speranza, J. Am. Chem. Soc. 1980, 102, 3120;
15. e) J. K. Kim, M. C. Caserio, J. Am. Chem. Soc. 1982, 104, 4624;
16. f) M. Attinà, F. Cacace, J. Am. Chem. Soc. 1983, 105, 1122;
17. g) M. C. Caserio, J. K. Kim, J. Am. Chem. Soc. 1983, 105, 6896;
18. h) N. A. Rahman, C. L. Fisher, M. C. Caserio, Org. Mass Spectrom. 1988, 23, 517;
19. i) T. Kotiaho, M. N. Eberlin, B. J. Shay, R. G. Cooks, J. Am. Chem. Soc. 1993, 115, 1004;
20. k) C. S. Creaser, B. L. Williamson, Eur. Mass Spectrom. 1998, 4, 103.
21. a) M. N. Eberlin, T. K. Majumdar, R. G. Cooks, J. Am. Chem. Soc. 1992, 114, 2884;
22. b) M. N. Eberlin, R. G. Cooks, J. Am. Chem. Soc. 1993, 115, 9226.
23. a) M. N. Eberlin, R. G. Cooks, Org. Mass Spectrom. 1993, 28, 679;
24. b) L. A. B. Moraes, F. C. Gozzo, M. N. Eberlin, P. Vainiotalo, J. Org. Chem. 1997, 62, 5096;
25. c) M. C. Carvalho, L. A. B. Moraes, C. Kascheres, M. N. Eberlin, J. Mass Spectrom. 1997, 32, 1137;
26. d) M. C. Carvalho, V. F. Juliano, C. Kascheres, M. N. Eberlin, J. Chem. Soc. Perkin Trans. 2 1997, 2347;
27. e) L. A. B. Moraes, M. N. Eberlin J. Am. Chem. Soc. 1998, 120, 11136;
28. f) M. Carvalho, F. C. Gozzo, M. A. Mendes, R. Sparrapan, C. Kascheres, M. N. Eberlin, Chem. Eur. J. 1998, 4, 1161;
29. g) F. Wang, S. Ma, W. A. Tao, R. G. Cooks, Angew. Chem. 1999, 111, 399; Angew. Chem. Int. Ed. 1999, 38, 386.
30. g) F. Wang, S. Ma, W. A. Tao, R. G. Cooks, Angew. Chem. 1999, 111, 399; Angew. Chem. Int. Ed. 1999, 38, 386.
31. L. A. B. Moraes, R. S. Pimpim, M. N. Eberlin, J. Org. Chem. 1996, 61, 8726.
32. H. Meerwein is best (and widely) known for his pioneering work on carbocations and alkyloxonium ions and for the widely used Meerwein's salts (see: a) H. Meerwein in Houben-Weyl Methoden der Organischen Chemie (Ed. : E. Müleer), Thieme Stuttgart, 1965, 4th ed. Vol. VI/3: Sauerstoffverbindungen I, p. 329;
33. b) H. Meerwein, G. Hinz, P. Hoffmann, E. Kroning, E. Pfeil, J. Prakt. Chem. 1937, 147, 257;
34. G. A. Olah, K. K. Laali, Q. Wang, G. K. Surya Prakash, Onium Ions, 1998, Wiley, New York), and for the Meerwein - Ponndorf - Verley - Oppenauer (MPVO) reduction (see: H. Meerwein, R. Schmidt, Liebigs Ann. Chem. 1925, 444, 221), a classical reaction that has also been studied and extended in the gas phase (see : D. Schröder, H. Schwarz, Angew. Chem. 1990, 102, 925; Angew. Chem. Int. Ed. Engl. 1990, 29, 910).
35. G. A. Olah, K. K. Laali, Q. Wang, G. K. Surya Prakash, Onium Ions, 1998, Wiley, New York), and for the Meerwein - Ponndorf - Verley - Oppenauer (MPVO) reduction (see: H. Meerwein, R. Schmidt, Liebigs Ann. Chem. 1925, 444, 221), a classical reaction that has also been studied and extended in the gas phase (see : D. Schröder, H. Schwarz, Angew. Chem. 1990, 102, 925; Angew. Chem. Int. Ed. Engl. 1990, 29, 910).
36. G. A. Olah, K. K. Laali, Q. Wang, G. K. Surya Prakash, Onium Ions, 1998, Wiley, New York), and for the Meerwein - Ponndorf - Verley - Oppenauer (MPVO) reduction (see: H. Meerwein, R. Schmidt, Liebigs Ann. Chem. 1925, 444, 221), a classical reaction that has also been studied and extended in the gas phase (see : D. Schröder, H. Schwarz, Angew. Chem. 1990, 102, 925; Angew. Chem. Int. Ed. Engl. 1990, 29, 910).
37. G. A. Olah, K. K. Laali, Q. Wang, G. K. Surya Prakash, Onium Ions, 1998, Wiley, New York), and for the Meerwein - Ponndorf - Verley - Oppenauer (MPVO) reduction (see: H. Meerwein, R. Schmidt, Liebigs Ann. Chem. 1925, 444, 221), a classical reaction that has also been studied and extended in the gas phase (see : D. Schröder, H. Schwarz, Angew. Chem. 1990, 102, 925; Angew. Chem. Int. Ed. Engl. 1990, 29, 910).
38. V. F. Juliano, C. Kascheres, F. C. Gozzo, M. N. Eberlin, C. L. Lago, Anal. Chem. 1996, 68, 1328.
39. T. O. Tiernan, J. H. Futrell, J. Phys. Chem. 1968, 72, 3080.
40. M. N. Eberlin, Mass Spectrom. Rev. 1997, 16, 113.
41. J. C. Schwartz, A. P. Wade, C. G. Enke, R. G. Cooks, Anal. Chem. 1990, 62, 1809.
42. Owing to the multiple collision conditions used for the ion - molecule reactions, proton transfer may occur from either the reactant ion, or from its products ions, or from both.
43. +=O, see refs. [8-10].
44. It is also noteworthy the similarities between the S/O replacement accomplished by the gas-phase Meerwein reaction/CID sequence (Scheme 6) with the classic reaction of thiourea with epoxides (Scheme 11) that forms thioepoxides and the O-analogue urea: a) J. F. Olin, F. B. Danis, J. Am. Chem. Soc. 1930, 52, 3322;
45. b) M. Sander, Chem. Rev. 1966, 66, 297. (equation presented)
46. 3 transacetalization/CID sequence, see : L. A. B. Moraes, M. N. Eberlin, J. Chem. Soc. Perkin Trans. 2 1997, 2105.
47. The electronic and ZPE energies of the species are available from the authors upon request.