Electron Transfer from a Cyclic Diaryliodine Species to Arenediazonium Salts. Evidence for the Intermediacy of 9-I-2 Structure in Inodine Atom Transfer Reactions

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6141-6145

  Geahigan, Karen B ^a   Taintor, Richard J ^a   George, Bindu M ^a   Meagher, Denise A ^a   Nalli, Thomas W ^b  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b Department of Computer Science   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000238467     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980113p     Document Type: Article

References (41)

1. This work was taken, in part, from the senior theses of K.B.G., R.J.T., B.M.G., and D.A.M. (a) Lake, K. B. B.S. Thesis, Purchase College, State University of New York (SUNY), 1990. (b) Taintor, R. J. B.A. Thesis, Purchase College, SUNY, 1992. (c) George, B. M. B.A. Thesis, Purchase College, SUNY, 1993. (d) Wenzel, D. A. B.A. Thesis, Purchase College, SUNY, 1993. Some of our results were presented previously: (e) Lake, K. B.; O'Donoghue, J.; Taintor, R. J.; Nalli, T. W. Book of Abstracts, Joint 44th Southeastern-26th Middle Atlantic Regional Meeting of the American Chemical Society, Alexandria, VA, December 1992; American Chemical Society: Washington, DC, 1992; Abstract 224. (f) Lake, K. B.; Taintor, R. J.; George, B. M.; Wenzel, D. A.; O'Donoghue, J.; Nalli, T. W. Abtracts of Papers, Part 2, 212th National Meeting of the American Chemical Society, Orlando, FL, Aug 25-29, 1996; American Chemical Society: Washington, DC, 1996; ORGN 366.
2. This work was taken, in part, from the senior theses of K.B.G., R.J.T., B.M.G., and D.A.M. (a) Lake, K. B. B.S. Thesis, Purchase College, State University of New York (SUNY), 1990. (b) Taintor, R. J. B.A. Thesis, Purchase College, SUNY, 1992. (c) George, B. M. B.A. Thesis, Purchase College, SUNY, 1993. (d) Wenzel, D. A. B.A. Thesis, Purchase College, SUNY, 1993. Some of our results were presented previously: (e) Lake, K. B.; O'Donoghue, J.; Taintor, R. J.; Nalli, T. W. Book of Abstracts, Joint 44th Southeastern-26th Middle Atlantic Regional Meeting of the American Chemical Society, Alexandria, VA, December 1992; American Chemical Society: Washington, DC, 1992; Abstract 224. (f) Lake, K. B.; Taintor, R. J.; George, B. M.; Wenzel, D. A.; O'Donoghue, J.; Nalli, T. W. Abtracts of Papers, Part 2, 212th National Meeting of the American Chemical Society, Orlando, FL, Aug 25-29, 1996; American Chemical Society: Washington, DC, 1996; ORGN 366.
3. This work was taken, in part, from the senior theses of K.B.G., R.J.T., B.M.G., and D.A.M. (a) Lake, K. B. B.S. Thesis, Purchase College, State University of New York (SUNY), 1990. (b) Taintor, R. J. B.A. Thesis, Purchase College, SUNY, 1992. (c) George, B. M. B.A. Thesis, Purchase College, SUNY, 1993. (d) Wenzel, D. A. B.A. Thesis, Purchase College, SUNY, 1993. Some of our results were presented previously: (e) Lake, K. B.; O'Donoghue, J.; Taintor, R. J.; Nalli, T. W. Book of Abstracts, Joint 44th Southeastern-26th Middle Atlantic Regional Meeting of the American Chemical Society, Alexandria, VA, December 1992; American Chemical Society: Washington, DC, 1992; Abstract 224. (f) Lake, K. B.; Taintor, R. J.; George, B. M.; Wenzel, D. A.; O'Donoghue, J.; Nalli, T. W. Abtracts of Papers, Part 2, 212th National Meeting of the American Chemical Society, Orlando, FL, Aug 25-29, 1996; American Chemical Society: Washington, DC, 1996; ORGN 366.
4. This work was taken, in part, from the senior theses of K.B.G., R.J.T., B.M.G., and D.A.M. (a) Lake, K. B. B.S. Thesis, Purchase College, State University of New York (SUNY), 1990. (b) Taintor, R. J. B.A. Thesis, Purchase College, SUNY, 1992. (c) George, B. M. B.A. Thesis, Purchase College, SUNY, 1993. (d) Wenzel, D. A. B.A. Thesis, Purchase College, SUNY, 1993. Some of our results were presented previously: (e) Lake, K. B.; O'Donoghue, J.; Taintor, R. J.; Nalli, T. W. Book of Abstracts, Joint 44th Southeastern-26th Middle Atlantic Regional Meeting of the American Chemical Society, Alexandria, VA, December 1992; American Chemical Society: Washington, DC, 1992; Abstract 224. (f) Lake, K. B.; Taintor, R. J.; George, B. M.; Wenzel, D. A.; O'Donoghue, J.; Nalli, T. W. Abtracts of Papers, Part 2, 212th National Meeting of the American Chemical Society, Orlando, FL, Aug 25-29, 1996; American Chemical Society: Washington, DC, 1996; ORGN 366.
5. This work was taken, in part, from the senior theses of K.B.G., R.J.T., B.M.G., and D.A.M. (a) Lake, K. B. B.S. Thesis, Purchase College, State University of New York (SUNY), 1990. (b) Taintor, R. J. B.A. Thesis, Purchase College, SUNY, 1992. (c) George, B. M. B.A. Thesis, Purchase College, SUNY, 1993. (d) Wenzel, D. A. B.A. Thesis, Purchase College, SUNY, 1993. Some of our results were presented previously: (e) Lake, K. B.; O'Donoghue, J.; Taintor, R. J.; Nalli, T. W. Book of Abstracts, Joint 44th Southeastern-26th Middle Atlantic Regional Meeting of the American Chemical Society, Alexandria, VA, December 1992; American Chemical Society: Washington, DC, 1992; Abstract 224. (f) Lake, K. B.; Taintor, R. J.; George, B. M.; Wenzel, D. A.; O'Donoghue, J.; Nalli, T. W. Abtracts of Papers, Part 2, 212th National Meeting of the American Chemical Society, Orlando, FL, Aug 25-29, 1996; American Chemical Society: Washington, DC, 1996; ORGN 366.
6. This work was taken, in part, from the senior theses of K.B.G., R.J.T., B.M.G., and D.A.M. (a) Lake, K. B. B.S. Thesis, Purchase College, State University of New York (SUNY), 1990. (b) Taintor, R. J. B.A. Thesis, Purchase College, SUNY, 1992. (c) George, B. M. B.A. Thesis, Purchase College, SUNY, 1993. (d) Wenzel, D. A. B.A. Thesis, Purchase College, SUNY, 1993. Some of our results were presented previously: (e) Lake, K. B.; O'Donoghue, J.; Taintor, R. J.; Nalli, T. W. Book of Abstracts, Joint 44th Southeastern-26th Middle Atlantic Regional Meeting of the American Chemical Society, Alexandria, VA, December 1992; American Chemical Society: Washington, DC, 1992; Abstract 224. (f) Lake, K. B.; Taintor, R. J.; George, B. M.; Wenzel, D. A.; O'Donoghue, J.; Nalli, T. W. Abtracts of Papers, Part 2, 212th National Meeting of the American Chemical Society, Orlando, FL, Aug 25-29, 1996; American Chemical Society: Washington, DC, 1996; ORGN 366.
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28. We also subjected 2,2′-diiododiphenylmethane (13) to reaction conditions which led to the transformation of 1 to 4 (i.e. same conditions as experiment 1, Table 1) but, interestingly, found no evidence for the formation of the six-member ring iodonium salt analogous to 4. This may be due to a failure of the 2-iododiphenylmethane-2′-yl radical to cyclize or to a failure of the electron transfer from the cyclized diaryliodine to the diazonium salt. The first possibility seems more likely because abstraction of the doubly benzylic hydrogens of the diiodide (13) is an additional competitive pathway available to the uncyclized iodoaryl radical in this system. Another factor may be that 4 is more stable than the corresponding six-member ring iodonium salt because of the potential participation of the iodine atom in the delocalized bonding of a 14-electron aromatic ring system. We thank a reviewer for pointing out the potential aromaticity of 4.
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