Highly efficient two-step synthesis of C-sp3-centered geminal diiodides

Organic Letters

Volumn 6, Issue 25, 2004, Pages 4731-4734

  Cloarec, Jean Manuel ^a   Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; DIETHYL 4 (HYDRAZINOSULFONYL)BENZYL PHOSPHONATE; IODINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; REDUCTION; SYNTHESIS;

EID: 11444251622     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047997l     Document Type: Article

References (52)

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20. 2, see: (f) Garcia Martinez, A.; Herrera Fernandez, A.; Martinez Alvarez, R.; García Fraile, A.; Bueno Calderon, J.; Osio Barcina, J. Synthesis 1986, 1076-1078. From a triple bond, see: (g) Aufauvre, L.; Marek, I.; Knochel, P. Chem. Commun. 1999, 2207-2208. From a diazo, see: (h) Neuman, R. C. Jr.; Rahm. M. L. J. Org. Chem. 1966, 31, 1857-1859. See also: (h) Pross. A.; Sternhell, S. Aust. J. Chem. 1970, 23, 989-1003.
21. 2, see: (f) Garcia Martinez, A.; Herrera Fernandez, A.; Martinez Alvarez, R.; García Fraile, A.; Bueno Calderon, J.; Osio Barcina, J. Synthesis 1986, 1076-1078. From a triple bond, see: (g) Aufauvre, L.; Marek, I.; Knochel, P. Chem. Commun. 1999, 2207-2208. From a diazo, see: (h) Neuman, R. C. Jr.; Rahm. M. L. J. Org. Chem. 1966, 31, 1857-1859. See also: (h) Pross. A.; Sternhell, S. Aust. J. Chem. 1970, 23, 989-1003.
22. 2, see: (f) Garcia Martinez, A.; Herrera Fernandez, A.; Martinez Alvarez, R.; García Fraile, A.; Bueno Calderon, J.; Osio Barcina, J. Synthesis 1986, 1076-1078. From a triple bond, see: (g) Aufauvre, L.; Marek, I.; Knochel, P. Chem. Commun. 1999, 2207-2208. From a diazo, see: (h) Neuman, R. C. Jr.; Rahm. M. L. J. Org. Chem. 1966, 31, 1857-1859. See also: (h) Pross. A.; Sternhell, S. Aust. J. Chem. 1970, 23, 989-1003.
23. 2, see: (f) Garcia Martinez, A.; Herrera Fernandez, A.; Martinez Alvarez, R.; García Fraile, A.; Bueno Calderon, J.; Osio Barcina, J. Synthesis 1986, 1076-1078. From a triple bond, see: (g) Aufauvre, L.; Marek, I.; Knochel, P. Chem. Commun. 1999, 2207-2208. From a diazo, see: (h) Neuman, R. C. Jr.; Rahm. M. L. J. Org. Chem. 1966, 31, 1857-1859. See also: (h) Pross. A.; Sternhell, S. Aust. J. Chem. 1970, 23, 989-1003.
24. 2, see: (f) Garcia Martinez, A.; Herrera Fernandez, A.; Martinez Alvarez, R.; García Fraile, A.; Bueno Calderon, J.; Osio Barcina, J. Synthesis 1986, 1076-1078. From a triple bond, see: (g) Aufauvre, L.; Marek, I.; Knochel, P. Chem. Commun. 1999, 2207-2208. From a diazo, see: (h) Neuman, R. C. Jr.; Rahm. M. L. J. Org. Chem. 1966, 31, 1857-1859. See also: (h) Pross. A.; Sternhell, S. Aust. J. Chem. 1970, 23, 989-1003.
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31. 2, pyridine, HCl, or NaOH in water. β-Elimination with DBU, see: Garcia Martinez, A.; Martinez Alvarez, R.; Martinez Gonzalez, S.; Subramanian, R. L.; Conrad, M. Tetrahedron Lett. 1992, 33, 2043-2044.
32. Using hv irradiation, see: (a) Miranda, M. A.; Perez-Prieto, J.; Font-Sanchis, E.; Scaiano, J. C. Acc. Chem. Res. 2001, 34, 717-726. See also: (b) Pienta, N. J.; Kropp, P. J. J. Am. Chem. Soc. 1978, 100, 655-657. Using LAH, see: (c) Ashby, E. C.; Deshpande, A. K. J. Org. Chem. 1994, 59, 3798-3805.
33. Using hv irradiation, see: (a) Miranda, M. A.; Perez-Prieto, J.; Font-Sanchis, E.; Scaiano, J. C. Acc. Chem. Res. 2001, 34, 717-726. See also: (b) Pienta, N. J.; Kropp, P. J. J. Am. Chem. Soc. 1978, 100, 655-657. Using LAH, see: (c) Ashby, E. C.; Deshpande, A. K. J. Org. Chem. 1994, 59, 3798-3805.
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37. For selected references for the synthesis of tri substituted gemdiiodoalkenes, see: (a) Gaviña, F.; Luis, S. V.; Ferrer, P.; Costero, A. M.; Marco, J. A. J. Chem. Res., Miniprint 1986, 2843-2852. (b) Dabdoub, M. J.; Dabdoub, V. B.; Baroni, A. C. M. J. Am. Chem. Soc. 2001, 123, 9694-9695. (c) Bonnet, B.; Le Gallic, Y.; Plé, G.; Duhamel, L. Synthesis 1993, 1071-1073.
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40. For ref see Supporting Information.
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42. Leading references, see: (a) Hünig, S.; Müller, H. R.; Thier, W. Angew. Chem., Int. Ed. Engl. 1965, 4, 271-280. (b) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91-155. Theorical studies for the outcome of diazene, see: (c) Pasto, D. J.; Chipman, D. M. J. Am. Chem. Soc. 1979, 101, 2290-2296. (d) Pasto, D. J. J. Am. Chem. Soc. 1979, 101, 6852-6857. (e) Tang, H. R.; McKee, M. L.; Stanbury, D. M. J. Am. Chem. Soc. 1995, 117, 8967-8973.
43. Leading references, see: (a) Hünig, S.; Müller, H. R.; Thier, W. Angew. Chem., Int. Ed. Engl. 1965, 4, 271-280. (b) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91-155. Theorical studies for the outcome of diazene, see: (c) Pasto, D. J.; Chipman, D. M. J. Am. Chem. Soc. 1979, 101, 2290-2296. (d) Pasto, D. J. J. Am. Chem. Soc. 1979, 101, 6852-6857. (e) Tang, H. R.; McKee, M. L.; Stanbury, D. M. J. Am. Chem. Soc. 1995, 117, 8967-8973.
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52. For the synthesis, see: (a) Herweh, J. J. Org. Chem. 1966, 31, 4308-4312. For blowing agent properties by thermal decomposition, see: (b) Herweh. J. U.S. Patent 3761544, 1973.