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Volumn 54, Issue 12, 1998, Pages 2763-2770

The effect of an alkoxy group on the kinetic and thermodynamic acidity of benzene and toluene

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXYBENZENE DERIVATIVE; BENZENE; REAGENT; TOLUENE; TOLUENE DERIVATIVE;

EID: 0032546279     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83011-1     Document Type: Article
Times cited : (32)

References (60)
  • 2
    • 84918129478 scopus 로고
    • Reviews : Schlosser, M.; Pure Appl. Chem. 1988, 60, 1627 - 1634; Mordini, A.; in Advances in Carbanion Chemistry (ed. : Snieckus, V.), Vol. I, Jai Press, Greenwich, 1992, pp. 1 - 44; Mordini, A.; in Comprehensive Organometallic Chemistry II (eds. : Abel, A.W.; Stone, F.G.A.; Wilkinson, G.), Vol. 11 (ed. : McKillop, A.), "Sodium and Potassium", Pergamon, Oxford 1995, pp. 93 - 128.
    • (1988) Pure Appl. Chem. , vol.60 , pp. 1627-1634
    • Schlosser, M.1
  • 3
    • 84918129478 scopus 로고
    • (ed. : Snieckus, V.), Jai Press, Greenwich
    • Reviews : Schlosser, M.; Pure Appl. Chem. 1988, 60, 1627 - 1634; Mordini, A.; in Advances in Carbanion Chemistry (ed. : Snieckus, V.), Vol. I, Jai Press, Greenwich, 1992, pp. 1 - 44; Mordini, A.; in Comprehensive Organometallic Chemistry II (eds. : Abel, A.W.; Stone, F.G.A.; Wilkinson, G.), Vol. 11 (ed. : McKillop, A.), "Sodium and Potassium", Pergamon, Oxford 1995, pp. 93 - 128.
    • (1992) Advances in Carbanion Chemistry , vol.1 , pp. 1-44
    • Mordini, A.1
  • 4
    • 84918129478 scopus 로고
    • (eds. : Abel, A.W.; Stone, F.G.A.; Wilkinson, G.), (ed. : McKillop, A.), "Sodium and Potassium", Pergamon, Oxford
    • Reviews : Schlosser, M.; Pure Appl. Chem. 1988, 60, 1627 - 1634; Mordini, A.; in Advances in Carbanion Chemistry (ed. : Snieckus, V.), Vol. I, Jai Press, Greenwich, 1992, pp. 1 - 44; Mordini, A.; in Comprehensive Organometallic Chemistry II (eds. : Abel, A.W.; Stone, F.G.A.; Wilkinson, G.), Vol. 11 (ed. : McKillop, A.), "Sodium and Potassium", Pergamon, Oxford 1995, pp. 93 - 128.
    • (1995) Comprehensive Organometallic Chemistry II , vol.11 , pp. 93-128
    • Mordini, A.1
  • 6
    • 33947459631 scopus 로고
    • 2-Methoxytoluene : Letsinger, R.L., Schnizer, A.W.; J. Org. Chem. 1951, 16, 869 - 873; Harmon, T.E.; Shirley, D.A.; J. Org. Chem. 1974, 39, 3164 - 3165.
    • (1951) J. Org. Chem. , vol.16 , pp. 869-873
    • Schnizer, A.W.1
  • 7
    • 0345333734 scopus 로고
    • 2-Methoxytoluene : Letsinger, R.L., Schnizer, A.W.; J. Org. Chem. 1951, 16, 869 - 873; Harmon, T.E.; Shirley, D.A.; J. Org. Chem. 1974, 39, 3164 - 3165.
    • (1974) J. Org. Chem. , vol.39 , pp. 3164-3165
    • Harmon, T.E.1    Shirley, D.A.2
  • 9
    • 0000171923 scopus 로고
    • 3-Methoxytoluene : Shirley, D.A.; Johnson, J.R.; Hendrix, J.P.; J. Organomet. Chem. 1968, 11, 209 - 216; Shirley, D.A.; Harmon, T.E.; Cheng, C.-f.; J. Organomet. Chem. 1974, 69, 327 - 344.
    • (1974) J. Organomet. Chem. , vol.69 , pp. 327-344
    • Shirley, D.A.1    Harmon, T.E.2    Cheng, C.-F.3
  • 10
    • 13144272984 scopus 로고
    • 4-Methoxytoluene : Lai, A.; Monduzzi, M.; Cabiddu, S.; Floris, C.; Melis, S.; Gazz. Chim. Ital. 1987, 117, 759 - 762; Chem. Abstr. 1988, 109, 148795c; see also : Letsinger, R.L.; Schnizer, A.W.; J. Org. Chem. 1951,16, 869 - 873; Slocum, D.W.; Thompson, J.; Friesen, C.; Tetrahedron Lett. 1995, 36, 8171 - 8174.
    • (1987) Gazz. Chim. Ital. , vol.117 , pp. 759-762
    • Lai, A.1    Monduzzi, M.2    Cabiddu, S.3    Floris, C.4    Melis, S.5
  • 11
    • 13144288102 scopus 로고
    • 4-Methoxytoluene : Lai, A.; Monduzzi, M.; Cabiddu, S.; Floris, C.; Melis, S.; Gazz. Chim. Ital. 1987, 117, 759 - 762; Chem. Abstr. 1988, 109, 148795c; see also : Letsinger, R.L.; Schnizer, A.W.; J. Org. Chem. 1951,16, 869 - 873; Slocum, D.W.; Thompson, J.; Friesen, C.; Tetrahedron Lett. 1995, 36, 8171 - 8174.
    • (1988) Chem. Abstr. , vol.109
  • 12
    • 33947459631 scopus 로고
    • 4-Methoxytoluene : Lai, A.; Monduzzi, M.; Cabiddu, S.; Floris, C.; Melis, S.; Gazz. Chim. Ital. 1987, 117, 759 - 762; Chem. Abstr. 1988, 109, 148795c; see also : Letsinger, R.L.; Schnizer, A.W.; J. Org. Chem. 1951,16, 869 - 873; Slocum, D.W.; Thompson, J.; Friesen, C.; Tetrahedron Lett. 1995, 36, 8171 - 8174.
    • (1951) J. Org. Chem. , vol.16 , pp. 869-873
    • Letsinger, R.L.1    Schnizer, A.W.2
  • 13
    • 0028863146 scopus 로고
    • 4-Methoxytoluene : Lai, A.; Monduzzi, M.; Cabiddu, S.; Floris, C.; Melis, S.; Gazz. Chim. Ital. 1987, 117, 759 - 762; Chem. Abstr. 1988, 109, 148795c; see also : Letsinger, R.L.; Schnizer, A.W.; J. Org. Chem. 1951,16, 869 - 873; Slocum, D.W.; Thompson, J.; Friesen, C.; Tetrahedron Lett. 1995, 36, 8171 - 8174.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8171-8174
    • Slocum, D.W.1    Thompson, J.2    Friesen, C.3
  • 14
    • 0006151415 scopus 로고
    • Schlosser, M.; Christmann, K.F.; Angew. Chem. 1964, 76, 683 - 684; Angew. Chem. Int. Ed. Engl. 1964, 3, 636, Schlosser, M.; Ladenberger, V.; Chem. Ber. 1967, 100, 3877 - 3892, spec. 3881.
    • (1964) Angew. Chem. , vol.76 , pp. 683-684
    • Schlosser, M.1    Christmann, K.F.2
  • 15
    • 84855830446 scopus 로고
    • Schlosser, M.; Christmann, K.F.; Angew. Chem. 1964, 76, 683 - 684; Angew. Chem. Int. Ed. Engl. 1964, 3, 636, Schlosser, M.; Ladenberger, V.; Chem. Ber. 1967, 100, 3877 - 3892, spec. 3881.
    • (1964) Angew. Chem. Int. Ed. Engl. , vol.3 , pp. 636
  • 16
    • 0342352142 scopus 로고
    • spec. 3881
    • Schlosser, M.; Christmann, K.F.; Angew. Chem. 1964, 76, 683 - 684; Angew. Chem. Int. Ed. Engl. 1964, 3, 636, Schlosser, M.; Ladenberger, V.; Chem. Ber. 1967, 100, 3877 - 3892, spec. 3881.
    • (1967) Chem. Ber. , vol.100 , pp. 3877-3892
    • Schlosser, M.1    Ladenberger, V.2
  • 17
    • 0000823084 scopus 로고
    • spec. 2604
    • Morton, A.A.; Hechenbleikner, I.; J. Am. Chem. Soc. 1936, 58, 2599 - 2605, spec. 2604; Lüttringhaus, G.; von Sääf, G.; Liebigs Ann. Chem. 1939, 542, 241 - 258; Wittig, G.; Benz, E.; Chem. Ber. 1958, 91, 874 - 882.
    • (1936) J. Am. Chem. Soc. , vol.58 , pp. 2599-2605
    • Morton, A.A.1    Hechenbleikner, I.2
  • 18
    • 84918649978 scopus 로고
    • Morton, A.A.; Hechenbleikner, I.; J. Am. Chem. Soc. 1936, 58, 2599 - 2605, spec. 2604; Lüttringhaus, G.; von Sääf, G.; Liebigs Ann. Chem. 1939, 542, 241 - 258; Wittig, G.; Benz, E.; Chem. Ber. 1958, 91, 874 - 882.
    • (1939) Liebigs Ann. Chem. , vol.542 , pp. 241-258
    • Lüttringhaus, G.1    Von Sääf, G.2
  • 19
    • 0000823084 scopus 로고
    • Morton, A.A.; Hechenbleikner, I.; J. Am. Chem. Soc. 1936, 58, 2599 - 2605, spec. 2604; Lüttringhaus, G.; von Sääf, G.; Liebigs Ann. Chem. 1939, 542, 241 - 258; Wittig, G.; Benz, E.; Chem. Ber. 1958, 91, 874 - 882.
    • (1958) Chem. Ber. , vol.91 , pp. 874-882
    • Wittig, G.1    Benz, E.2
  • 21
    • 0000769164 scopus 로고
    • Wittig, G.; Pockels, U.; Dröge, H.; Ber. Dtsch. Chem. Ges. 1938, 71, 1903 - 1912; Gilman, H.; Bebb, R.L.; J. Am. Chem. Soc. 1939, 61, 109 - 112.
    • (1939) J. Am. Chem. Soc. , vol.61 , pp. 109-112
    • Gilman, H.1    Bebb, R.L.2
  • 23
    • 0343786699 scopus 로고
    • Morton, A.A.; J. Am. Chem. Soc. 1947, 69, 969 - 971; Ireland, R.E.; Thompson, W.J.; Tetrahedron Lett. 1979, 20, 4705 - 4708.
    • (1947) J. Am. Chem. Soc. , vol.69 , pp. 969-971
    • Morton, A.A.1
  • 25
    • 0004219714 scopus 로고
    • (ed. : Schlosser, M.), Wiley, Chichester, spec. 98 - 104
    • Schlosser, M.; in Organometallics in Synthesis : A Manual (ed. : Schlosser, M.), Wiley, Chichester, 1994, pp. 1 - 166, spec. 98 - 104.
    • (1994) Organometallics in Synthesis : A Manual , pp. 1-166
    • Schlosser, M.1
  • 27
    • 0003472060 scopus 로고
    • Dissociation Constants of Organic Bases in Aqueous Solution
    • Butterworth, London
    • Perrin, D.; Dissociation Constants of Organic Bases in Aqueous Solution (Supplement to Pure Appl. Chem.), Butterworth, London, 1965.
    • (1965) Pure Appl. Chem. , Issue.SUPPL.
    • Perrin, D.1
  • 28
    • 84987082416 scopus 로고
    • Klumpp, G.W.; Recl. Trav. Chim. Pays-Bas 1986, 105, 1 - 21; see also : Fraser, R.R.; Bresse, M.; Mansour, T.S.; J. Chem. Soc., Chem. Commun, 1983, 620 - 621.
    • (1986) Recl. Trav. Chim. Pays-Bas , vol.105 , pp. 1-21
    • Klumpp, G.W.1
  • 30
  • 32
    • 33847088063 scopus 로고
    • Summerhays, K.D.; Pollack, S.K.; Taft, R.W.; Hehre, W.J.; J. Am. Chem. Soc. 1977, 99, 4585 - 4594; Tagapeera, M.; Summerhays, K.D.; Hehre, W.J.; Topsom, R.D.; Pross, A.; Radom, L.; Taft, R.W.; J. Org. Chem. 1981, 46, 891 - 903; Meot-Ner (Mautner), M.; Sieck, L.W.; J. Am. Chem. Soc. 1991, 113, 4448 - 4460.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 4585-4594
    • Summerhays, K.D.1    Pollack, S.K.2    Taft, R.W.3    Hehre, W.J.4
  • 34
    • 0000273461 scopus 로고
    • Summerhays, K.D.; Pollack, S.K.; Taft, R.W.; Hehre, W.J.; J. Am. Chem. Soc. 1977, 99, 4585 - 4594; Tagapeera, M.; Summerhays, K.D.; Hehre, W.J.; Topsom, R.D.; Pross, A.; Radom, L.; Taft, R.W.; J. Org. Chem. 1981, 46, 891 - 903; Meot-Ner (Mautner), M.; Sieck, L.W.; J. Am. Chem. Soc. 1991, 113, 4448 - 4460.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4448-4460
    • Meot-Ner, M.1    Sieck, L.W.2
  • 36
    • 0004142591 scopus 로고
    • Van Nostrand Reinhold, London
    • Gillespie, R.J.; Molecular Geometry, Van Nostrand Reinhold, London, 1972; Gillespie, R.J.; Hargittai, I.; The VSEPR Model of Molecular Geometry, Allyn and Bacon, Boston, 1991.
    • (1972) Molecular Geometry
    • Gillespie, R.J.1
  • 41
    • 0027515047 scopus 로고
    • Faigl, F.; Schlosser, M.; Tetrahedron 1993, 49, 10271 - 10278; Schlosser, M.; Keller, H.; Liebigs Ann. Chem. 1995, 1587 - 1589; Desponds, O.; Schlosser, M.; J. Organomet. Chem. 1996, 507, 257 - 261.
    • (1993) Tetrahedron , vol.49 , pp. 10271-10278
    • Faigl, F.1    Schlosser, M.2
  • 42
    • 0002497233 scopus 로고
    • Faigl, F.; Schlosser, M.; Tetrahedron 1993, 49, 10271 - 10278; Schlosser, M.; Keller, H.; Liebigs Ann. Chem. 1995, 1587 - 1589; Desponds, O.; Schlosser, M.; J. Organomet. Chem. 1996, 507, 257 - 261.
    • (1995) Liebigs Ann. Chem. , pp. 1587-1589
    • Schlosser, M.1    Keller, H.2
  • 43
    • 0030600637 scopus 로고    scopus 로고
    • Faigl, F.; Schlosser, M.; Tetrahedron 1993, 49, 10271 - 10278; Schlosser, M.; Keller, H.; Liebigs Ann. Chem. 1995, 1587 - 1589; Desponds, O.; Schlosser, M.; J. Organomet. Chem. 1996, 507, 257 - 261.
    • (1996) J. Organomet. Chem. , vol.507 , pp. 257-261
    • Desponds, O.1    Schlosser, M.2
  • 55
    • 13144281551 scopus 로고
    • Cannizzaro, S.; Liebigs Ann. Chem. 1861, 117, 238 - 247; Li, P.; Alper, H.; J. Org. Chem. 1986, 51, 4354 - 4356
    • (1861) Liebigs Ann. Chem. , vol.117 , pp. 238-247
    • Cannizzaro, S.1
  • 56
    • 0000585542 scopus 로고
    • Cannizzaro, S.; Liebigs Ann. Chem. 1861, 117, 238 - 247; Li, P.; Alper, H.; J. Org. Chem. 1986, 51, 4354 - 4356
    • (1986) J. Org. Chem. , vol.51 , pp. 4354-4356
    • Li, P.1    Alper, H.2
  • 59
    • 0343165241 scopus 로고
    • (ed. : Müller, E.), Thieme Verlag, Stuttgart, spec. 144
    • Huisgen, R.; Houben-Weyl : Methoden der organischen Chemie (ed. : Müller, E.), Thieme Verlag, Stuttgart, 1955, Vol. 3/1, 99 - 162, spec. 144.
    • (1955) Houben-Weyl : Methoden der Organischen Chemie , vol.3 , Issue.1 , pp. 99-162
    • Huisgen, R.1


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