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Synthesis 2007(19): 2979-2986
DOI: 10.1055/s-2007-990776
DOI: 10.1055/s-2007-990776
PAPER
© Georg Thieme Verlag Stuttgart · New York
A New Approach to the Synthesis of Vicinal Iodoperoxyalkanes by the Reaction of Alkenes with Iodine and Hydroperoxides
Further Information
Received
24 April 2007
Publication Date:
11 September 2007 (online)
Publication History
Publication Date:
11 September 2007 (online)
Abstract
A convenient procedure was developed for the synthesis of vicinal iodoperoxyalkanes by the reaction of alkenes with iodine and hydroperoxides. The best results were achieved with the use of excess iodine. The replacement of one iodine atom by hydroperoxides in vicinal diiodoalkanes was discovered. A suggestion was made about the reaction mechanism.
Key words
iodination - peroxidation - hydrogen peroxide - tert-butyl hydroperoxide - iodoperoxyalkanes
-
1a
Jefford CW. Adv. Drug Res. 1997, 29: 271 -
1b
McCullough KJ.Nojima M. Curr. Org. Chem. 2001, 5: 631 -
1c
Dong Y. Mini-Rev. Med. Chem. 2002, 2: 113 -
1d
Jefford CW.Boukouvalas AJJ. Synthesis 1988, 391 -
1e
Vennerstrom JL.Fu H.-N.Ellis WY.Ager AL.Wood JK.Andersen SL.Gerena L.Milhous WK. J. Med. Chem. 1992, 35: 3023 -
1f
Dong Y.Matile H.Chollet J.Kaminsky R.Wood JK.Vennerstrom JL. J. Med. Chem. 1999, 42: 1477 -
1g
Todovovic NM.Stefanovic M.Tinant B.Declercq J.-P.Makler MT.Solaja BA. Steroids 1996, 61: 688 -
1h
Dong Y.Vennerstrom JL. J. Org. Chem. 1998, 63: 8582 -
1i
Kim H.-S.Tsuchiya K.Shibata Y.Wataya Y.Ushigoe Y.Masuyama A.Nojima M.McCullough K. J. Chem. Soc., Perkin Trans. 1 1999, 1867 -
1j
Kim H.-S.Shibata Y.Wataya Y.Tsuchiya K.Masuyama A.Nojima M. J. Med. Chem. 1999, 42: 2604 -
1k
Opsenica D.Pocsfalvi G.Juranic Z.Tinant B.Declercq J.-P.Kyle DE.Milhous WK.olaja BA. J. Med. Chem. 2000, 43: 3274 -
1l
Šolaja BA.Terzić N.Pocsfalvi G.Genena L.Tinant B.Opsenica D.Milhous WK. J. Med. Chem. 2002, 45: 3331 -
1m
Dong Y.Vennerstrom JL. J. Heterocycl. Chem. 2001, 38: 463 -
1n
McCullough KJ.Nonami Y.Masuyama A.Nojima M.Kim H.-S.Wataya Y. Tetrahedron Lett. 1999, 40: 9151 -
1o
McCullough KJ.Wood JK.Bhattacharjee AK.Dong Y.Kyle DE.Milhous WK.Vennerstrom JL. J. Med. Chem. 2000, 43: 1246 -
1p
Griesbaum K.Övez B.Huh TS.Dong Y. Liebigs Ann. Chem. 1995, 1571 -
1q
Griesbaum K.Liu X.Kassiaris A.Scherer M. Liebigs Ann./Recl. 1997, 1381 -
1r
Vennerstrom JL.Arbe B.Brun SR.Charman SA.Chiu FCK.Chollet J.Dong Y.Dorn A.Hunziker D.Matile H.McIntosh K.Padmanilayam M.Tomas JS.Scheurer C.Scorneaux B.Tang Y.Urwyler H.Wittlin S.Charman WN. Nature (London) 2004, 430: 900 -
1s
mitek K.Zupan M.Stavber S.Iskra J. Org. Lett. 2006, 8: 2491 -
2a
Posner GH.O’Neill PM. Acc. Chem. Res. 2004, 37: 397 -
2b
Klayman DL. Science 1985, 228: 1049 -
2c
White NJ.Nosten F.Looareesuwan S.Watkins WM.Marsh K.Snow RW.Kokwaro G.Ouma J.Hien TT.Molyneux ME.Taylor TE.Newbold CI.Ruebush TK.Danis M.Greenwood BM.Anderson M.Olliaro P. Lancet 1999, 353: 1965 -
3a
Posner GH.Cumming JN.Ploypradith P.Chang HO. J. Am. Chem. Soc. 1995, 117: 5885 -
3b
Posner GH.Parker MH.Northrop J.Elias JS.Ploypradith P.Xie S.Shapiro TA. J. Med. Chem. 1999, 42: 300 -
3c
O’Neill PM.Searle NL.Kan KW.Storr RC.Maggs JL.Ward SA.Raynes K.Park BK. J. Med. Chem. 1999, 42: 5487 -
4a
Davidson BS. J. Org. Chem. 1991, 56: 6722 -
4b
Sandler JS.Colin PL.Hooper JNA.Faulkner DJ. J. Nat. Prod. 2002, 65: 1258 -
4c
Rudi A.Afanii R.Gravalos LG.Aknin M.Gaydou E.Vacelet J.Kashman Y. J. Nat. Prod. 2003, 66: 682 -
5a
Ramirez A.Woerpel KA. Org. Lett. 2005, 7: 4617 -
5b
Tokuyasu T.Kunikawa S.McCullough KJ.Masuyama A.Nojima M. J. Org. Chem. 2005, 70: 251 -
5c
Dai P.Trullinger TK.Liu X.Dussault PH. J. Org. Chem. 2006, 71: 2283 -
5d
Dussault PH.Liu X. Org. Lett. 1999, 1: 1391 -
5e
Dussault PH.Trullinger TK.Noor-e-Ain F. Org. Lett. 2002, 4: 4591 -
5f
Bloodworth AJ.Bothwell BD.Collins AN.Maidwell NL. Tetrahedron Lett. 1996, 37: 1885 -
5g
Zhang Q.Jin HX.Liu H.-H.Wu Y.-K. Chin. J. Chem. 2006, 24: 1190 -
6a
Jones CW. Applications of Hydrogen Peroxides and Derivatives Royal Society of Chemistry; Cambridge: 1999. -
6b
The Chemistry of Peroxides
Patai S. Wiley; New York: 1983. -
6c
Organic Peroxides
Ando W. Wiley; New York: 1992. -
6d
Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer
Adam W. Wiley-VCH; Weinheim: 2000. -
6e
Catalytic Oxidations with Hydrogen Peroxide as Oxidant
Strukul G. Kluwer Academic; Boston, MA: 1992. -
7a
Bloodworth AJ.Bowyer AJ.Mitchell JC. J. Org. Chem. 1986, 51: 1790 -
7b
Bloodworth AJ.Griffin IM. J. Chem. Soc., Perkin Trans. 1 1974, 688 -
7c
Schmitz E.Rieche A.Brede O. J. Prakt. Chem. 1970, 312: 30 -
8a
Kopecky KR.Filby JE.Mumford C.Lockwood PA.Ding J.-Y. Can. J. Chem. 1975, 53: 1103 -
8b
Kopecky KR.Scott WA.Lockwood PA.Mumford C. Can. J. Chem. 1978, 56: 1114 -
8c
Kopecky KR.Lockwood PA.Gomez RR.Ding J.-Y. Can. J. Chem. 1981, 59: 851 -
8d
Kopecky KR.Miller AJ. Can. J. Chem. 1984, 62: 1840 -
9a
Kim H.-S.Begum K.Ogura N.Wataya Y.Tokuyasu T.Masuyama A.Nojima M.McCullough KJ. J. Med. Chem. 2002, 45: 4732 -
9b
Tokuyasu T.Masuyama A.Nojima M.Kim H.-S.Wataya Y. Tetrahedron Lett. 2000, 41: 3145 -
9c
Tokuyasu T.Masuyama A.Nojima M.McCullough KJ. J. Org. Chem. 2000, 65: 1069 -
9d
Nonami Y.Tokuyasu T.Masuyama A.Nojima M.McCullogh KJ.Kim H.-S.Wataya Y. Tetrahedron Lett. 2000, 41: 4681 -
9e
Ito T.Tokuyasu T.Masuyama A.Nojima M.McCullough KJ. Tetrahedron 2003, 59: 525 -
9f
McCullough KJ.Ito T.Tokuyasu T.Masuyama A.Nojima M. Tetrahedron Lett. 2001, 42: 5529 -
10a
Bloodworth AJ.Curtis R J. J. Chem. Soc., Chem. Commun. 1989, 173 -
10b
Bloodworth AJ.Curtis RJ.Mistry N . J. Chem. Soc., Chem. Commun. 1989, 954 -
10c
Ushigoe Y.Kano Y.Nojima M. J. Chem. Soc., Perkin Trans. 1 1997, 5 - 11
Dussault PH.Davies DR. Tetrahedron Lett. 1996, 37: 463 - 12
Bloodworth AJ.Spencer MD. Tetrahedron Lett. 1990, 31: 5513 - 13
Ahmed A.Dussault PH. Tetrahedron 2005, 61: 4657 -
14a
Barluenga J.Marco-Arias M.Gonzalez-Bobes F.Ballesteros A.Gonzalez JM. Chem. Eur. J. 2004, 7: 1677 -
14b
Sabitha G.Babu SR.Rajkumar M.Reddy ChS.Yadav JS. Tetrahedron Lett. 2001, 42: 3955 -
14c
Yadav JS.Reddy BVS.Baishya G.Harshavardhan SJ.Chary ChJ.Gupta MK. Tetrahedron Lett. 2005, 46: 3569 -
14d
Sanseverino AM.de Mattos MCS. Synthesis 1998, 1584 -
15a
De La Mare PBD.Bolton R. Electrophilic Additions to Unsaturated Systems Elsevier; London: 1966. -
15b
Jensen FR.Coleman WE. J. Org. Chem. 1958, 23: 869 -
15c
Zanger M.Rabinowitz JL. J. Org. Chem. 1975, 40: 248 - 16
Saito I.Nagata R.Yuba K.Matsuura T. Tetrahedron Lett. 1983, 24: 1737 - 17
Antonovsky VL.Buzlanova MM. Analytical Chemistry of Organic Peroxides (in Russian) Chimia; Moscow: 1978. - 18
Stone H.Shechter H. Org. Synth. 1951, 31: 66 - 19
Greengard H. Org. Synth. 1932, 12: 26 - 20
Antonovsky VL.Khursan SL. Physical Chemistry of Organic Peroxides (in Russian) PTC Akademkniga; Moscow: 2003. - 21
Zyk NV.Beloglazkina EK.Sosonyuk SE.Bulanov MN.Chudinov YuB. Russ. Chem. Bull. 2000, 49: 1557 ; Izv. Akad. Nauk Ser. Khim. 2000, 1569 - 22
Barluenga J.Rodriguez MA.Campos PJ. J. Chem. Soc., Perkin Trans. 1 1990, 2807 - 23
Ballard DH.Bloodworth AJ.Bunce RJ. J. Chem. Soc. D 1969, 815 - 24
Khan M.Agarwal R.Ahmad S.Ahmad F.Osman SM. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1988, 27: 430