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Volumn 62, Issue 15, 1997, Pages 5096-5103

Transacetalization with acylium ions. A structurally diagnostic ion/molecule reaction for cyclic acetals and ketals in the gas phase

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; 1,3 DITHIOLANE DERIVATIVE; 1,3 OXATHIOLANE DERIVATIVE; ACETAL DERIVATIVE; OXYGEN 18;

EID: 0030833838     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970116m     Document Type: Article
Times cited : (59)

References (43)
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    • For details and recent examples of the application of pentaquadrupole mass spectrometry to the study of gas phase ion/molecule reactions, see: (a) Eberlin, M. N.; Kotiaho, T.; Shay, B. J.; Yang, S. S.; Cooks, R. G. J. Am. Chem. Soc. 1994, 116, 2457. (b) Gozzo, F. C.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 1995, 6, 554. (c) Gozzo, F. C.; Eberlin, M. N. J. Mass Spectrom. 1995, 30, 1553. (d) Gozzo, F. C.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 1995, 6, 554. (e) Sorrilha, A. E. P. M.; Pimpim, R. S.; Gozzo, F. C.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 1996, 7, 1126. (f) Eberlin, M. N.; Sorrilha, A. E. P. M.; Gozzo, F. C.; Pimpim, R. S. J. Am. Chem. Soc. 1997, 119, 3550. (g) Eberlin, M. N. Mass Spectrom. Rev. In press.
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    • In press
    • For details and recent examples of the application of pentaquadrupole mass spectrometry to the study of gas phase ion/molecule reactions, see: (a) Eberlin, M. N.; Kotiaho, T.; Shay, B. J.; Yang, S. S.; Cooks, R. G. J. Am. Chem. Soc. 1994, 116, 2457. (b) Gozzo, F. C.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 1995, 6, 554. (c) Gozzo, F. C.; Eberlin, M. N. J. Mass Spectrom. 1995, 30, 1553. (d) Gozzo, F. C.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 1995, 6, 554. (e) Sorrilha, A. E. P. M.; Pimpim, R. S.; Gozzo, F. C.; Eberlin, M. N. J. Am. Soc. Mass Spectrom. 1996, 7, 1126. (f) Eberlin, M. N.; Sorrilha, A. E. P. M.; Gozzo, F. C.; Pimpim, R. S. J. Am. Chem. Soc. 1997, 119, 3550. (g) Eberlin, M. N. Mass Spectrom. Rev. In press.
    • Mass Spectrom. Rev.
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  • 29
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    • 6O)" net additions. Moreover, transacetalization also describes the reaction more precisely by indicating the type of mechanism that operates and the class of product (cyclic "ionic ketals") that are formed, whereas pointing out the interesting correlation with the analogous condensed phase transacetalization reactions.
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    • note
    • 5 and it can be easily generated at high yields from several precursors such as ethyl vinyl ketone.
  • 39
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    • note
    • The term "structure" is used in a restricted sense, to denote connectivity rather than detailed structure.
  • 40
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    • note
    • Structurally diagnostic ion/molecule reactions and triple-stage mass spectrometry have shown that the cyclic 2-methyl-1,3-dioxolanylium ion forms almost exclusively (99%) the acetyl cation upon collision-induced dissociation, see ref 4b. Therefore, similar behavior is expected for the other homologous and derivatives.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.