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Synlett 2004(12): 2131-2134
DOI: 10.1055/s-2004-832803
DOI: 10.1055/s-2004-832803
LETTER
© Georg Thieme Verlag Stuttgart · New York
Lone Selectivity of the Decatungstate-Sensitized Photooxidation of 1-Substituted Cycloalkenes
Further Information
Received
6 July 2004
Publication Date:
03 September 2004 (online)
Publication History
Publication Date:
03 September 2004 (online)
Abstract
Decatungstate-sensitized oxidation of alkyl and phenyl substituted cycloalkenes in the presence of molecular oxygen shows a general preference for hydrogen abstraction on the congested side of the double bond.
Key words
photooxidation - cycloalkenes - hydroperoxides - decatungstate - polyoxometalate
-
1a
Schenck GO. Ind. Eng. Chem. 1963, 55: 40 -
1b
Gollnick K. Adv. Photochem. 1968, 6: 1 -
1c
Foote CS. Science 1968, 162: 963 -
1d
Wasserman HH.Murray RW. Singlet Oxygen Academic Press; New York: 1979. -
1e
Tanielian C.Mechin R.Seghrouchni R.Schweitzer C. Photochem. Photobiol. 2000, 71: 12 -
2a
Araki Y.Dobrowolski DC.Goyne TE.Hanson DC.Jiang ZQ.Lee KJ.Foote CS. J. Am. Chem. Soc. 1984, 106: 4570 -
2b
Foote CS. Tetrahedron 1985, 41: 2221 -
2c
Eriksen J.Foote CS. J. Am. Chem. Soc. 1980, 102: 6083 -
3a
Tanielian C.Schweitzer C.Seghrouchni R.Esch M.Mechin R. Photochem. Photobiol. Sci. 2003, 2: 297 -
3b
Tanielian C.Seghrouchni R.Schweitzer C. J. Phys. Chem. A 2003, 107: 1102 -
4a
Stratakis M.Orfanopoulos M. Tetrahedron 2000, 56: 1595 -
4b
Stephenson LM.Grdina MB.Orfanopoulos M. Acc. Chem. Res. 1980, 13: 419 -
5a A special issue of chemical reviews is devoted to polyoxometalates:
Hill CL. Chem. Rev. 1998, 98: 1 -
5b
Hill CL.Christina M.McCartha P. Coord. Chem. Rev. 1995, 143: 407 -
5c
Neumann R. Prog. Inorg. Chem. 1998, 47: 317 -
5d
Papaconstantinou E. Chem. Soc. Rev. 1989, 18: 1 -
5e
Hiskia A.Mylonas A.Papaconstantinou E. Chem. Soc. Rev. 2001, 30: 62 - 6
Tanielian C. Coord. Chem. Rev. 1998, 180: 1165 -
7a
Duncan DC.Netzel TL.Hill CL. Inorg. Chem. 1995, 34: 4640 -
7b
Texier I.Delouis JF.Delaire JA.Giannotti C.Plaza P.Martin MM. Chem. Phys. Lett. 1999, 311: 139 -
8a
Renneke RF.Pasquali M.Hill CL. J. Am. Chem. Soc. 1990, 112: 6585 -
8b
Prosser-McCartha CM.Hill CL. J. Am. Chem. Soc. 1990, 112: 3671 -
8c
Dondi D.Fagnoni M.Molinari A.Maldotti A.Albini A. Chem.-Eur. J. 2004, 10: 142 -
9a
Texier I.Delaire JA.Giannotti C. Phys. Chem. Chem. Phys. 2000, 2: 1205 -
9b
Ermolenko LP.Delaire JA.Giannotti C. J. Chem. Soc., Perkin Trans. 2 1997, 25 -
9c
Giannotti C.Richter C. Trends Photochem. Photobiol. 1997, 4: 43 -
9d
Kothe T.Martschke R.Fischer H. J. Chem. Soc., Perkin Trans. 2 1998, 503 -
10a
Maldotti A.Amadelli R.Carassiti V.Molinari A. Inorg. Chim. Acta 1997, 256: 309 -
10b
Molinari A.Amadelli R.Mazzacani A.Sartori G.Maldotti A. Langmuir 2002, 18: 5400 - 11
Tanielian C.Duffy K.Jones A. J. Phys. Chem. B 1997, 101: 4276 - 12
Lykakis NI.Tanielian C.Orfanopoulos M. Org. Lett. 2003, 5: 2875 - 13
Duncan DC.Fox MA. J. Phys. Chem. A 1998, 102: 4559 -
14a
Molinari A.Amadelli R.Carassiti V.Maldotti A. Eur. J. Inorg. Chem. 2000, 91 -
14b
Yamase T.Usami T. J. Chem. Soc., Dalton Trans. 1988, 183 -
15a
Orfanopoulos M.Stratakis M.Elemes Y. J. Am. Chem. Soc. 1990, 112: 6417 -
15b
Stratakis M.Orfanopoulos M. Synth. Commun. 1993, 23: 425 - 16 For the terminology lone, twin and twix see:
Adam W.Bottke N.Krebs O. J. Am. Chem. Soc. 2000, 122: 6791 - 17
Font-Sanchis E.Aliaga C.Bejan EV.Cornejo R.Scaiano JC. J. Org. Chem. 2003, 68: 3199 - 18
Croft AK.Easton CJ.Radom L. J. Am. Chem. Soc. 2003, 125: 4119 -
19a
Cadwell SE.Porter NA. J. Am. Chem. Soc. 1995, 117: 8676 -
19b
Lowe JR.Porter NA. J. Am. Chem. Soc. 1997, 119: 11534