The role of ate complexes in halogen(metalloid)-metal exchange reactions: A theoretical study

European Journal of Organic Chemistry

Volumn , Issue 9, 1998, Pages 1851-1860

  Boche, Gernot ^a   Schimeczek, Michael ^a,b   Cioslowski, Jerzy ^a,b   Piskorz, Pawel ^b  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b FLORIDA STATE UNIVERSITY   (United States)

Author keywords

Ate complexes; Halogen(metalloid) metal exchange reactions; Theoretical study

Indexed keywords

EID: 0001139430     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199809)1998:9<1851::aid-ejoc1851>3.0.co;2-n     Document Type: Article

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26. D. Seebach, N. Peleties, Angew Chem. 1969, 81, 465; Angew. Chem. Int. Ed. Engl. 1969, 8, 450. - D. Seebach, N. Peleties, Chem. Ber 1972, 705, 511-520; D. Seebach, A. K. Beck, Angew. Chem. 1974, 86, 859-860; Angew. Chem. Int. Ed. Engl. 1974, 13, 806; W. Dumont, P. Bayet, A. Krief, Angew. Chem. 1974, 86, 857-858; Angew. Chem. Int. Ed. Engl. 1974, 13, 804; W. Dumont, A. Krief, Angew. Chem. 1975, 87, 347-348; Angew. Chem. Int. Ed. Engl. 1975, 14, 350; A. Krief. Tetrahedron 1980, 36, 2531-2640; J. N. Denis, A. Krief, Tetrahedron Lett. 1982, 23, 3411-3414. - M. Clarembeau, A. Krief, Tetrahedron Lett. 1984, 25, 3629-3632; M. Clarembeau, A. Krief, Tetrahedron Lett. 1985, 26, 1093-1096; C. Paulmeier in Selenium Reagents and Intermediates in Organometallic Chemistry (Ed.: J. E. Baldwin), Pergamon Press, New York, 1986, p. 105, 260; H. J. Reich in Organoselenium Chemistry (Ed.: D. Liotts), WileyInterscience, New York 1987, ch. 5.
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35. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
36. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
37. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
38. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
39. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
40. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
41. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
42. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
43. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
44. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
45. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
46. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
47. D. Hellwinkel, G. Fahrbach, Chem. Ber. 1968, 101, 574-584; D. Seebach. A. K. Beck, Chem. Ber. 1975, 108, 314-321; T. Kauffmann, H. Ahlers, Chem. Ber. 1983, 116, 1001-1008: T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem 1987, 99, 1221-1222; Angew. Chem. Int. Ed. Engl. 1987, 26, 1187; S. M. Barros, J. V. Comassetto, J. Berriel, Tetrahedron Lett 1989, 30, 7353-7356; T. Hiiro, Y. Mogami, N. Kambe, S.-I. Fujiwara, N. Sonoda, Synth. Commun. 1990, 20, 703-709; T. Hiiro, Y. Monta, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am Chem. Soc. 1990, 112, 455-457; T. Hiiro, Y. Atarashi, N. Kambe, S.-I. Fujiwara, A. Ogawa, I. Ryu, N. Sonoda, Organometallics 1990, 9, 1355-1357; A. Maercker, H. Bodenstedt, L. Brandsma, Angew. Chem. 1992, 104, 1387-1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1339; L. Engman, D. Stern, Organometallics 1993, 12, 1445-1448; T. Kanda, S. Kato, T. Sugmo, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
48. D. Seyferth, M. A. Weiner, L G. Vaughan, G. Raab, D. E. Welch, H. M. Cohen, D. L. Alleston, Bull. Soc. Chim. Fr. 1963, 1364-1367; D. Seyferth, G. J. Murphy, B. J. Mauzé, J. Am Chem. Soc. 1977, 99, 5317-5330; D. Seyferth, K. R. Wursthorn, J. Organomet Chem. 1977, 137, C17-C21; D. Seyferth, S. C. Vick, J. Organomet. Chem. 1978, 144, 1-12; W. C. Still, J. Am. Chem. Soc. 1978, 100, 1481-1487; N. Meyer, D. Seebach, Chem Ber. 1980, 113, 1290-1303. - R. J. Goswami, J. Am. Chem Soc. 1980, 102, 5973-5974; E. Piers, V. Karumarante, J. Org. Chem. 1983, 48, 1774-1776; J. S. Sawyer, T. L. Macdonald, J. G. McGarvey, J. Am Chem. Soc. 1984, 106, 3376-3377. - H. J. Reich, K. E. Yelm, I. L. Reich, J. Org. Chem. 1984, 49, 3438-3440; D. Farah, T. J. Karol, H. G. Kuivila, Organometallics 1985, 4, 662-666; M. Pereyre, J.-P. Quitard, A. Rahm, Tin in Organic Synthesis, Butterworths, London 1987, 149-184; A. J. Ashe III, S. Mahmoud, Organometallies 1988, 7, 1878-1880; A. J. Ashe III, L. L. Lohr, S. M. Al-Taweel, Organometallics 1991, 10, 2424-2431.
49. D. Seyferth, M. A. Weiner, L G. Vaughan, G. Raab, D. E. Welch, H. M. Cohen, D. L. Alleston, Bull. Soc. Chim. Fr. 1963, 1364-1367; D. Seyferth, G. J. Murphy, B. J. Mauzé, J. Am Chem. Soc. 1977, 99, 5317-5330; D. Seyferth, K. R. Wursthorn, J. Organomet Chem. 1977, 137, C17-C21; D. Seyferth, S. C. Vick, J. Organomet. Chem. 1978, 144, 1-12; W. C. Still, J. Am. Chem. Soc. 1978, 100, 1481-1487; N. Meyer, D. Seebach, Chem Ber. 1980, 113, 1290-1303. - R. J. Goswami, J. Am. Chem Soc. 1980, 102, 5973-5974; E. Piers, V. Karumarante, J. Org. Chem. 1983, 48, 1774-1776; J. S. Sawyer, T. L. Macdonald, J. G. McGarvey, J. Am Chem. Soc. 1984, 106, 3376-3377. - H. J. Reich, K. E. Yelm, I. L. Reich, J. Org. Chem. 1984, 49, 3438-3440; D. Farah, T. J. Karol, H. G. Kuivila, Organometallics 1985, 4, 662-666; M. Pereyre, J.-P. Quitard, A. Rahm, Tin in Organic Synthesis, Butterworths, London 1987, 149-184; A. J. Ashe III, S. Mahmoud, Organometallies 1988, 7, 1878-1880; A. J. Ashe III, L. L. Lohr, S. M. Al-Taweel, Organometallics 1991, 10, 2424-2431.
50. D. Seyferth, M. A. Weiner, L G. Vaughan, G. Raab, D. E. Welch, H. M. Cohen, D. L. Alleston, Bull. Soc. Chim. Fr. 1963, 1364-1367; D. Seyferth, G. J. Murphy, B. J. Mauzé, J. Am Chem. Soc. 1977, 99, 5317-5330; D. Seyferth, K. R. Wursthorn, J. Organomet Chem. 1977, 137, C17-C21; D. Seyferth, S. C. Vick, J. Organomet. Chem. 1978, 144, 1-12; W. C. Still, J. Am. Chem. Soc. 1978, 100, 1481-1487; N. Meyer, D. Seebach, Chem Ber. 1980, 113, 1290-1303. - R. J. Goswami, J. Am. Chem Soc. 1980, 102, 5973-5974; E. Piers, V. Karumarante, J. Org. Chem. 1983, 48, 1774-1776; J. S. Sawyer, T. L. Macdonald, J. G. McGarvey, J. Am Chem. Soc. 1984, 106, 3376-3377. - H. J. Reich, K. E. Yelm, I. L. Reich, J. Org. Chem. 1984, 49, 3438-3440; D. Farah, T. J. Karol, H. G. Kuivila, Organometallics 1985, 4, 662-666; M. Pereyre, J.-P. Quitard, A. Rahm, Tin in Organic Synthesis, Butterworths, London 1987, 149-184; A. J. Ashe III, S. Mahmoud, Organometallies 1988, 7, 1878-1880; A. J. Ashe III, L. L. Lohr, S. M. Al-Taweel, Organometallics 1991, 10, 2424-2431.
51. D. Seyferth, M. A. Weiner, L G. Vaughan, G. Raab, D. E. Welch, H. M. Cohen, D. L. Alleston, Bull. Soc. Chim. Fr. 1963, 1364-1367; D. Seyferth, G. J. Murphy, B. J. Mauzé, J. Am Chem. Soc. 1977, 99, 5317-5330; D. Seyferth, K. R. Wursthorn, J. Organomet Chem. 1977, 137, C17-C21; D. Seyferth, S. C. Vick, J. Organomet. Chem. 1978, 144, 1-12; W. C. Still, J. Am. Chem. Soc. 1978, 100, 1481-1487; N. Meyer, D. Seebach, Chem Ber. 1980, 113, 1290-1303. - R. J. Goswami, J. Am. Chem Soc. 1980, 102, 5973-5974; E. Piers, V. Karumarante, J. Org. Chem. 1983, 48, 1774-1776; J. S. Sawyer, T. L. Macdonald, J. G. McGarvey, J. Am Chem. Soc. 1984, 106, 3376-3377. - H. J. Reich, K. E. Yelm, I. L. Reich, J. Org. Chem. 1984, 49, 3438-3440; D. Farah, T. J. Karol, H. G. Kuivila, Organometallics 1985, 4, 662-666; M. Pereyre, J.-P. Quitard, A. Rahm, Tin in Organic Synthesis, Butterworths, London 1987, 149-184; A. J. Ashe III, S. Mahmoud, Organometallies 1988, 7, 1878-1880; A. J. Ashe III, L. L. Lohr, S. M. Al-Taweel, Organometallics 1991, 10, 2424-2431.
52. D. Seyferth, M. A. Weiner, L G. Vaughan, G. Raab, D. E. Welch, H. M. Cohen, D. L. Alleston, Bull. Soc. Chim. Fr. 1963, 1364-1367; D. Seyferth, G. J. Murphy, B. J. Mauzé, J. Am Chem. Soc. 1977, 99, 5317-5330; D. Seyferth, K. R. Wursthorn, J. Organomet Chem. 1977, 137, C17-C21; D. Seyferth, S. C. Vick, J. Organomet. Chem. 1978, 144, 1-12; W. C. Still, J. Am. Chem. Soc. 1978, 100, 1481-1487; N. Meyer, D. Seebach, Chem Ber. 1980, 113, 1290-1303. - R. J. Goswami, J. Am. Chem Soc. 1980, 102, 5973-5974; E. Piers, V. Karumarante, J. Org. Chem. 1983, 48, 1774-1776; J. S. Sawyer, T. L. Macdonald, J. G. McGarvey, J. Am Chem. Soc. 1984, 106, 3376-3377. - H. J. Reich, K. E. Yelm, I. L. Reich, J. Org. Chem. 1984, 49, 3438-3440; D. Farah, T. J. Karol, H. G. Kuivila, Organometallics 1985, 4, 662-666; M. Pereyre, J.-P. Quitard, A. Rahm, Tin in Organic Synthesis, Butterworths, London 1987, 149-184; A. J. Ashe III, S. Mahmoud, Organometallies 1988, 7, 1878-1880; A. J. Ashe III, L. L. Lohr, S. M. Al-Taweel, Organometallics 1991, 10, 2424-2431.
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189. R. J. Gillespie, R. S. Nyholm, Q. Rev. Chem. Soc. 1957, II, 339-380; A. W. Searcy, J Chem. Phys. 1958, 28, 1237-1242; J. Chem. Phys. 1959, 31, 1-4; R. J. Gillespie, J. Am. Chem. Soc. 1960, 82, 5978-5983; R. J. Gillespie, J. Chem. Educ. 1963, 40, 259-301; J. Chem. Educ. 1970, 47, 18-23; R. J. Gillespie, Angew. Chem. 1967, 79, 885-896; Angew. Chem. Int. Ed. Engl. 1967, 6, 819; R. J. Gillespie, E. A. Robinson, Angew. Chem. 1996, 108, 539-560; Angew. Chem. Int. Ed. Engl. 1996, 35, 495-514.
190. R. J. Gillespie, R. S. Nyholm, Q. Rev. Chem. Soc. 1957, II, 339-380; A. W. Searcy, J Chem. Phys. 1958, 28, 1237-1242; J. Chem. Phys. 1959, 31, 1-4; R. J. Gillespie, J. Am. Chem. Soc. 1960, 82, 5978-5983; R. J. Gillespie, J. Chem. Educ. 1963, 40, 259-301; J. Chem. Educ. 1970, 47, 18-23; R. J. Gillespie, Angew. Chem. 1967, 79, 885-896; Angew. Chem. Int. Ed. Engl. 1967, 6, 819; R. J. Gillespie, E. A. Robinson, Angew. Chem. 1996, 108, 539-560; Angew. Chem. Int. Ed. Engl. 1996, 35, 495-514.
191. Strictly speaking, among the ate anions considered in this paper, only those of Cl, Br and I are hypervalent according to the quantitative criterion published in: J. Cioslowski, S. T. Mixon, Inorg. Chem. 1993, 32, 3209-3216.
192. T. Kanda, S. Kato, N. Kambe, Y. Kohara, N. Sonoda, J. Phys. Org. Chem. 1996, 9, 29-34. The authors have not specified whether Bu stands for nBu, sBu or tBu.
193. 2O raises the energy of the reactant adduct and lowers the energy of the transition state. We became aware of the work of these authors after having finished our investigations.
194. D. E. Applequist, D. F. O'Brien, J. Am. Chem. Soc. 1963, 85, 743-748.
195. The phenyl anion is predicted to detach more easily than the vinyl anion, while experimentally the formation of the latter appears to be favoured see ref.
196. This result, however, might be attributable to the different solvation energies and degrees of aggregation of vinyllithium and phenyllithium, respectively, see ref.[7i].
197. V. Schulze, M. Brönstrup, V. P. W. Böhm, P. Schwerdtfeger, M. Schimeczek, R. W. Hoffmann, Angew. Chem. 1998, 110, 869-871; Angew. Chem Int. Ed. 1998, 37, 824-826.
198. V. Schulze, M. Brönstrup, V. P. W. Böhm, P. Schwerdtfeger, M. Schimeczek, R. W. Hoffmann, Angew. Chem. 1998, 110, 869-871; Angew. Chem Int. Ed. 1998, 37, 824-826.
199. M. Müller, R. W. Hoffmann, unpublished results.
200. In a forthcoming publication, we will deal in detail with the effect of the counterion on the structures and energies of ate anions.