Evidence for extended π,n-participation in solvolysis of some benzyl chlorides

Journal of Physical Organic Chemistry

Volumn 16, Issue 12, 2003, Pages 900-904

  Jurić, Sandra ^a   Filipović, Anita ^a   Kronja, Olga ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

,n participation; Benzyl chlorides; Solvolysis

Indexed keywords

ACTIVATION ANALYSIS; ALCOHOLS; CHLORINE COMPOUNDS; CHROMATOGRAPHIC ANALYSIS; IMPURITIES; SILICA GEL; SUBSTITUTION REACTIONS; SUBSTRATES; SYNTHESIS (CHEMICAL);

ELECTRON STABILIZATION; SOLVOLYSIS; TRANSITION STATES;

AROMATIC COMPOUNDS;

EID: 0345724738     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.687     Document Type: Article

References (27)

1. Bartlett PA, Braumann JI, Johnson WS, Volkmann RA. J. Am. Chem. Soc. 1973; 95: 7502-7504.
2. (a) Kronja O, Polla E, Borči S. J. Chem. Soc., Chem. Commun. 1983; 1044-1045;
3. (b) Borči S, Humski K, Imper V, Kronja O, Orlović M, Polla E. J. Chem. Soc. Perkin Trans. 1 1989; 1861-1861;
4. (c) Kronja O, Orlović M, Humski K, Borči S. J. Am. Chem. Soc. 1991; 113: 2306-2308.
5. Malnar I, Humski K, Kronja O. J. Org. Chem. 1998; 63: 3041-3044.
6. Malnar I, Jurič S, Vrček V, Gjuranovč Æ, Mihalič Z, Kronja O. J. Org. Chem. 2002; 67: 1490-1495.
7. JurÊ S, Kronja O. J. Phys. Org. Chem. 2002; 15: 556-560.
8. (a) Biegeleisen J, Wolfsberg M. Adv. Chem. Phys. 1958; 1:15;
9. (b) Melander L. Isotope Effects on Reaction Rates. Ronald Press: New York, 1960;
10. (c) Collins CI, Bowman NS. Isotope Effects in Chemical Reactions. ACS Monograph 167. Van Nostrand Reinhold: New York, 1970;
11. (d) Wolfsberg M. Acc. Chem. Res. 1972; 7: 225-233;
12. (e) Melander L, Saunders WH, Jr. Reaction Rates of Isotopic Molecules. Wiley: New York, 1980.
13. (a) Ho Nh, Noble WJ. J. Org. Chem. 1989; 54: 2018-2021;
14. (b) Johnson WS, Telfer SJ, Cheng S, Schubert U. J. Am. Chem. Soc. 1987; 109: 2517-2518, and Refs 10 and 13 cited therein.
15. (a) Isaacs N. Physical Organic Chemistry (2nd edn). Longman: London, 1995; 146-192, 451-455, 650-654;
16. (b) Ruasse MF, Argile A, Dubois JE. J. Am. Chem. Soc. 1984; 106: 4846-4849;
17. (c) Hammett LP. Physical Organic Chemistry. McGraw-Hill: New York, 1970;
18. (d) Brown HC, Okamoto Y. J. Am. Chem. Soc. 1958; 80: 4979-4987.
19. (a) Richard JP, Amyes TL, Vontor T. J. Am. Chem. Soc. 1991; 113: 5871-5873;
20. (b) Toteva MM, Richard JP. J. Am. Chem. Soc. 1996; 118: 11434-11445;
21. (c) Richard JP, Toteva MM, Amyes TL. Org. Lett. 2001; 3: 2225-2228.
22. (a) Bentley TW, Carter GE. J. Am. Chem. Soc. 1982; 104: 5741-5747;
23. (b) Kevill DN, D'Souza MJ. J. Chem. Res. (S) 1993; 174-175.
24. Mihel I, Orlović M, Polla E, Borči S. J. Org. Chem. 1979; 44: 4086-4090.
25. Mihel I, Šistek J, Borči S, Humski K, Sunko DE. J. Org. Chem. 1979; 44: 4091-4096.
26. Page MI. Chem. Soc. Rev. 1973; 295-323.
27. Shiner VJ, Jr, Buddenbaum WE, Murr BL, Lamaty G. J. Am. Chem. Soc. 1968; 90: 418-426.