Evidence for divalent iodine (9-I-2) radical intermediates in the thermolysis of (tert-butylperoxy)iodanes. An unusually efficient deiodination of o-iodocumyl alcohols by cyclohexyl radicals

Journal of the American Chemical Society

Volumn 119, Issue 11, 1997, Pages 2628-2632

  Dolenc, Darko ^a   Plesničar, Božo ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOIODINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HYDROLYSIS; IN VITRO STUDY; REACTION ANALYSIS; TEMPERATURE;

EID: 1842377426     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9636404     Document Type: Article

References (53)

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9. For thermally or photoinitiated chlorinations by (dichloro)iodobenzenes, see: (a) Russell, G. A. J. Am. Chem. Soc. 1958, 80, 4987. (b) Banks, D. F.; Huyser, E. S.; Kleinburg, J. J. Org. Chem. 1964, 29, 3692 (c) Chlorinations by [chloro(tert-butoxy)iodo]benzene: Tanner, D. D.; Gidley, G. C. J. Am. Chem. Soc. 1968, 90, 808. (d) Chlorinations by the Martin's chloroiodanes: Amey, R. L.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 3060. J. Org. Chem. 1979, 44, 1779. (e) For the Breslow's template-directed chlorination of steroids, see: Breslow, R.; Corcoran, R.; Dale, J. A. Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842, and references therein. (f) For anchimeric acceleration of ortho-iodo-substituded peroxides homolysis, see, for example: Martin, J. C. ACS Symp. Ser. 1978, 69, 71, and references cited therein.
10. For thermally or photoinitiated chlorinations by (dichloro)iodobenzenes, see: (a) Russell, G. A. J. Am. Chem. Soc. 1958, 80, 4987. (b) Banks, D. F.; Huyser, E. S.; Kleinburg, J. J. Org. Chem. 1964, 29, 3692 (c) Chlorinations by [chloro(tert-butoxy)iodo]benzene: Tanner, D. D.; Gidley, G. C. J. Am. Chem. Soc. 1968, 90, 808. (d) Chlorinations by the Martin's chloroiodanes: Amey, R. L.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 3060. J. Org. Chem. 1979, 44, 1779. (e) For the Breslow's template-directed chlorination of steroids, see: Breslow, R.; Corcoran, R.; Dale, J. A. Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842, and references therein. (f) For anchimeric acceleration of ortho-iodo-substituded peroxides homolysis, see, for example: Martin, J. C. ACS Symp. Ser. 1978, 69, 71, and references cited therein.
11. For thermally or photoinitiated chlorinations by (dichloro)iodobenzenes, see: (a) Russell, G. A. J. Am. Chem. Soc. 1958, 80, 4987. (b) Banks, D. F.; Huyser, E. S.; Kleinburg, J. J. Org. Chem. 1964, 29, 3692 (c) Chlorinations by [chloro(tert-butoxy)iodo]benzene: Tanner, D. D.; Gidley, G. C. J. Am. Chem. Soc. 1968, 90, 808. (d) Chlorinations by the Martin's chloroiodanes: Amey, R. L.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 3060. J. Org. Chem. 1979, 44, 1779. (e) For the Breslow's template-directed chlorination of steroids, see: Breslow, R.; Corcoran, R.; Dale, J. A. Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842, and references therein. (f) For anchimeric acceleration of ortho-iodo-substituded peroxides homolysis, see, for example: Martin, J. C. ACS Symp. Ser. 1978, 69, 71, and references cited therein.
12. For thermally or photoinitiated chlorinations by (dichloro)iodobenzenes, see: (a) Russell, G. A. J. Am. Chem. Soc. 1958, 80, 4987. (b) Banks, D. F.; Huyser, E. S.; Kleinburg, J. J. Org. Chem. 1964, 29, 3692 (c) Chlorinations by [chloro(tert-butoxy)iodo]benzene: Tanner, D. D.; Gidley, G. C. J. Am. Chem. Soc. 1968, 90, 808. (d) Chlorinations by the Martin's chloroiodanes: Amey, R. L.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 3060. J. Org. Chem. 1979, 44, 1779. (e) For the Breslow's template-directed chlorination of steroids, see: Breslow, R.; Corcoran, R.; Dale, J. A. Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842, and references therein. (f) For anchimeric acceleration of ortho-iodo-substituded peroxides homolysis, see, for example: Martin, J. C. ACS Symp. Ser. 1978, 69, 71, and references cited therein.
13. For thermally or photoinitiated chlorinations by (dichloro)iodobenzenes, see: (a) Russell, G. A. J. Am. Chem. Soc. 1958, 80, 4987. (b) Banks, D. F.; Huyser, E. S.; Kleinburg, J. J. Org. Chem. 1964, 29, 3692 (c) Chlorinations by [chloro(tert-butoxy)iodo]benzene: Tanner, D. D.; Gidley, G. C. J. Am. Chem. Soc. 1968, 90, 808. (d) Chlorinations by the Martin's chloroiodanes: Amey, R. L.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 3060. J. Org. Chem. 1979, 44, 1779. (e) For the Breslow's template-directed chlorination of steroids, see: Breslow, R.; Corcoran, R.; Dale, J. A. Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842, and references therein. (f) For anchimeric acceleration of ortho-iodo-substituded peroxides homolysis, see, for example: Martin, J. C. ACS Symp. Ser. 1978, 69, 71, and references cited therein.
14. For thermally or photoinitiated chlorinations by (dichloro)iodobenzenes, see: (a) Russell, G. A. J. Am. Chem. Soc. 1958, 80, 4987. (b) Banks, D. F.; Huyser, E. S.; Kleinburg, J. J. Org. Chem. 1964, 29, 3692 (c) Chlorinations by [chloro(tert-butoxy)iodo]benzene: Tanner, D. D.; Gidley, G. C. J. Am. Chem. Soc. 1968, 90, 808. (d) Chlorinations by the Martin's chloroiodanes: Amey, R. L.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 3060. J. Org. Chem. 1979, 44, 1779. (e) For the Breslow's template-directed chlorination of steroids, see: Breslow, R.; Corcoran, R.; Dale, J. A. Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842, and references therein. (f) For anchimeric acceleration of ortho-iodo-substituded peroxides homolysis, see, for example: Martin, J. C. ACS Symp. Ser. 1978, 69, 71, and references cited therein.
15. For thermally or photoinitiated chlorinations by (dichloro)iodobenzenes, see: (a) Russell, G. A. J. Am. Chem. Soc. 1958, 80, 4987. (b) Banks, D. F.; Huyser, E. S.; Kleinburg, J. J. Org. Chem. 1964, 29, 3692 (c) Chlorinations by [chloro(tert-butoxy)iodo]benzene: Tanner, D. D.; Gidley, G. C. J. Am. Chem. Soc. 1968, 90, 808. (d) Chlorinations by the Martin's chloroiodanes: Amey, R. L.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 3060. J. Org. Chem. 1979, 44, 1779. (e) For the Breslow's template-directed chlorination of steroids, see: Breslow, R.; Corcoran, R.; Dale, J. A. Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842, and references therein. (f) For anchimeric acceleration of ortho-iodo-substituded peroxides homolysis, see, for example: Martin, J. C. ACS Symp. Ser. 1978, 69, 71, and references cited therein.
16. For thermally or photoinitiated chlorinations by (dichloro)iodobenzenes, see: (a) Russell, G. A. J. Am. Chem. Soc. 1958, 80, 4987. (b) Banks, D. F.; Huyser, E. S.; Kleinburg, J. J. Org. Chem. 1964, 29, 3692 (c) Chlorinations by [chloro(tert-butoxy)iodo]benzene: Tanner, D. D.; Gidley, G. C. J. Am. Chem. Soc. 1968, 90, 808. (d) Chlorinations by the Martin's chloroiodanes: Amey, R. L.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 3060. J. Org. Chem. 1979, 44, 1779. (e) For the Breslow's template-directed chlorination of steroids, see: Breslow, R.; Corcoran, R.; Dale, J. A. Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842, and references therein. (f) For anchimeric acceleration of ortho-iodo-substituded peroxides homolysis, see, for example: Martin, J. C. ACS Symp. Ser. 1978, 69, 71, and references cited therein.
17. Tanner, D. D.; Reed, D. W.; Setiloane, B. P. J. Am. Chem. Soc. 1982, 104, 3917, and references cited therein.
18. (a) Banks, J. T.; Garcia, H.; Miranda, M. A.; Perez-Prieto, J.; Scaiano, J. C. J. Am. Chem. Soc. 1995, 117, 5049.
19. (b) For a previous attempt to detect such an intermediate, see: Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1990, 55, 1061.
20. (a) Ochiai, M.; Ito, T.; Masaki, Y.; Shiro, M. J. J. Am. Chem. Soc. 1992, 114, 6269.
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22. (c) See also: Ochiai, M.; Ito, T.; Shiro, M. J. Chem. Soc. Chem. Commun. 1993, 218.
23. Moss et al. have prepared 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one by a ligand exchange of a labile (phosphoryloxy)iodane (prepared in situ by the reaction of 1-chloro-1,2-benziodoxol-3(1H)-one with silver diphenyl phosphate in DMSO) with tert-butyl hydroperoxide. Moss, R. A.; Zhang, H. J. Am. Chem. Soc. 1994, 116, 4471.
24. [Bis(tert-butylperoxy)iodo]benzene was proposed as an intermediate in the low-temperature reaction of iodosobenzene with tert-butyl hydroperoxide, and its decomposition to iodobenzene and tert-butylperoxyl radicals has been reported. When the reaction was run in diethyl ether, good yields of tert-butylperoxy acetal were isolated. Milas, N. A.; Plesničar, B. J. Am. Chem. Soc. 1968, 90, 4450. See, also: Traylor, T. G.; Xu, F. J. Am. Chem. Soc. 1987, 109, 6201. (b) [Bis(benzoylperoxy)iodo]benzenes were isolated as amorphous, labile (rather hazardous) materials: Plesničar, B.; Russell, G. A. Angew. Chem., Int. Ed. Engl. 1970, 9, 797. Plesničar, B. J. Org. Chem. 1975, 40, 3267.
25. [Bis(tert-butylperoxy)iodo]benzene was proposed as an intermediate in the low-temperature reaction of iodosobenzene with tert-butyl hydroperoxide, and its decomposition to iodobenzene and tert-butylperoxyl radicals has been reported. When the reaction was run in diethyl ether, good yields of tert-butylperoxy acetal were isolated. Milas, N. A.; Plesničar, B. J. Am. Chem. Soc. 1968, 90, 4450. See, also: Traylor, T. G.; Xu, F. J. Am. Chem. Soc. 1987, 109, 6201. (b) [Bis(benzoylperoxy)iodo]benzenes were isolated as amorphous, labile (rather hazardous) materials: Plesničar, B.; Russell, G. A. Angew. Chem., Int. Ed. Engl. 1970, 9, 797. Plesničar, B. J. Org. Chem. 1975, 40, 3267.
26. [Bis(tert-butylperoxy)iodo]benzene was proposed as an intermediate in the low-temperature reaction of iodosobenzene with tert-butyl hydroperoxide, and its decomposition to iodobenzene and tert-butylperoxyl radicals has been reported. When the reaction was run in diethyl ether, good yields of tert-butylperoxy acetal were isolated. Milas, N. A.; Plesničar, B. J. Am. Chem. Soc. 1968, 90, 4450. See, also: Traylor, T. G.; Xu, F. J. Am. Chem. Soc. 1987, 109, 6201. (b) [Bis(benzoylperoxy)iodo]benzenes were isolated as amorphous, labile (rather hazardous) materials: Plesničar, B.; Russell, G. A. Angew. Chem., Int. Ed. Engl. 1970, 9, 797. Plesničar, B. J. Org. Chem. 1975, 40, 3267.
27. [Bis(tert-butylperoxy)iodo]benzene was proposed as an intermediate in the low-temperature reaction of iodosobenzene with tert-butyl hydroperoxide, and its decomposition to iodobenzene and tert-butylperoxyl radicals has been reported. When the reaction was run in diethyl ether, good yields of tert-butylperoxy acetal were isolated. Milas, N. A.; Plesničar, B. J. Am. Chem. Soc. 1968, 90, 4450. See, also: Traylor, T. G.; Xu, F. J. Am. Chem. Soc. 1987, 109, 6201. (b) [Bis(benzoylperoxy)iodo]benzenes were isolated as amorphous, labile (rather hazardous) materials: Plesničar, B.; Russell, G. A. Angew. Chem., Int. Ed. Engl. 1970, 9, 797. Plesničar, B. J. Org. Chem. 1975, 40, 3267.
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35. 4) to be 1.55 ± 0.15 kcal/mol (Bourassa-Bataille, H.; Sauvageau, P.; Sandorfy, C. Can. J. Chem. 1963, 41, 2240. Carlson, G. L.; Fateley, W. G.; Manocha, A. S.; Bentley, F. F. J. Phys. Chem. 1972, 76, 1553). Theoretical studies have indicated that the intramolecular interactions in the cis conformer of o-halophenols are due to a competition between the attractive and repulsive H⋯halogen interactions, as well as the O⋯halogen repulsions. An important factor is also the O-H⋯X angle (Dietrich, S. W.; Jorgensen, E. C.; Kollman, P. A.; Rothenberg, S. J. Am. Chem. Soc. 1976, 98, 8310). Since this angle is near to 180° in the six-membered hydrogen-bonded ring in o-iodocumyl alcohols, i.e., the optimal value for such interactions (it is around 141° in o-iodophenol), it seems safe to predict that the strength of the intramolecular hydrogen bonding in these compounds must be ≥2 kcal/mol.
36. 4) to be 1.55 ± 0.15 kcal/mol (Bourassa-Bataille, H.; Sauvageau, P.; Sandorfy, C. Can. J. Chem. 1963, 41, 2240. Carlson, G. L.; Fateley, W. G.; Manocha, A. S.; Bentley, F. F. J. Phys. Chem. 1972, 76, 1553). Theoretical studies have indicated that the intramolecular interactions in the cis conformer of o-halophenols are due to a competition between the attractive and repulsive H⋯halogen interactions, as well as the O⋯halogen repulsions. An important factor is also the O-H⋯X angle (Dietrich, S. W.; Jorgensen, E. C.; Kollman, P. A.; Rothenberg, S. J. Am. Chem. Soc. 1976, 98, 8310). Since this angle is near to 180° in the six-membered hydrogen-bonded ring in o-iodocumyl alcohols, i.e., the optimal value for such interactions (it is around 141° in o-iodophenol), it seems safe to predict that the strength of the intramolecular hydrogen bonding in these compounds must be ≥2 kcal/mol.
37. 4) to be 1.55 ± 0.15 kcal/mol (Bourassa-Bataille, H.; Sauvageau, P.; Sandorfy, C. Can. J. Chem. 1963, 41, 2240. Carlson, G. L.; Fateley, W. G.; Manocha, A. S.; Bentley, F. F. J. Phys. Chem. 1972, 76, 1553). Theoretical studies have indicated that the intramolecular interactions in the cis conformer of o-halophenols are due to a competition between the attractive and repulsive H⋯halogen interactions, as well as the O⋯halogen repulsions. An important factor is also the O-H⋯X angle (Dietrich, S. W.; Jorgensen, E. C.; Kollman, P. A.; Rothenberg, S. J. Am. Chem. Soc. 1976, 98, 8310). Since this angle is near to 180° in the six-membered hydrogen-bonded ring in o-iodocumyl alcohols, i.e., the optimal value for such interactions (it is around 141° in o-iodophenol), it seems safe to predict that the strength of the intramolecular hydrogen bonding in these compounds must be ≥2 kcal/mol.
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