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Synlett 2005(16): 2407-2419
DOI: 10.1055/s-2005-917087
DOI: 10.1055/s-2005-917087
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Recent Developments in the Chemistry of Quinoneimides
Weitere Informationen
Received
18 May 2005
Publikationsdatum:
21. September 2005 (online)
Publikationsverlauf
Publikationsdatum:
21. September 2005 (online)

Abstract
This account describes the developments in quinoneimide chemistry during the last two decades, emphasizing the addition of weak nucleophilic systems leading to cycloadducts in most cases.
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1 Introduction
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2 Synthesis and Stability
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3 Chemistry of Quinoneimides
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3.1 Addition Reactions of Quinoneimides
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3.2 Cycloaddition/Cyclization Reactions of Quinoneimides
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4 Conclusion
Key words
quinoneimides - addition reactions - Diels-Alder reactions - cyclization reactions - dipolar cycloaddition reactions
- 1
Patai S.Rappoport Z. The Chemistry of Quinonoid Compounds Part I and II, Vol. 2: John Wiley & Sons; New York: 1988. -
2a
Nair V.Kumar S. Synlett 1996, 1143 -
2b
Magdziak D.Meek SJ.Pettus TRR. Chem. Rev. 2004, 104: 1383 - 3
Tong LKJ. The Theory of Photographic Process Part II, 4th ed.:James TH. Macmillan; New York: 1977. Chap. 12. -
4a
Corbett JF. J. Soc. Cosmet. Chem. 1973, 24: 103 -
4b
Brown KC.Corbett JF. J. Soc. Cosmet. Chem. 1979, 30: 191 -
4c
Corbett JF. J. Soc. Cosmet. Chem. 1984, 35: 297 - 5
Holmes TJ.Lawton RG. J. Am. Chem. Soc. 1977, 99: 1984 - 6
Finley KT.Tong LKJ. In The Chemistry of the Carbon-Nitrogen Double BondPatai S. John Wiley & Sons; London: 1970. Chap. 14. - 7
Brown ER. In The Chemistry of Quinonoid CompoundsPatai S.Rappoport Z. John Wiley & Sons; New York: 1988. Chap. 21. - 8
Friedrichsen W.Bottcher A. Heterocycles 1981, 16: 1009 -
9a
Willstätter R.Mayer E. Chem. Ber. 1904, 37: 1494 -
9b
Willstätter R.Pfannenstiel A. Chem. Ber. 1904, 3: 4605 - 10
Adams R.Nagarkatti AS. J. Am. Chem. Soc. 1950, 72: 4601 - 11
Adams R.Winnick CN. J. Am. Chem. Soc. 1951, 73: 5687 - 12
Engler TA.Chai W.Lynch O. Tetrahedron Lett. 1995, 36: 7003 - 13
Adams R.Way JW. J. Am. Chem. Soc. 1954, 76: 2763 - 14
Adams R.Wankel RA. J. Am. Chem. Soc. 1951, 73: 2219 - 15
Nickel U.Jaenicke W. Ber. Bunsen-Ges. Phys. Chem. 1982, 86: 695 - 16
Nickel U.Haase E.Jaenicke W. Ber. Bunsen-Ges. Phys. Chem. 1977, 81: 849 - 17
Ramachandran MS.Vivekanandam TS.Subbaratnam NR.Rajaram A. Indian J. Chem., Sect. A: Inorg., Bio-inorg., Phys., Theor. Anal. Chem. 1983, 22: 897 - 18
Moore HE.Garmendia MJ.Cooper W. J. Environ. Sci. Technol. 1984, 18: 348 - 19
Bezverkhii N.Zinukhov VD.Kremlov MM. Zh. Org. Khim. 1984, 20: 339 - 20
Adams R.Reifschneider W. Bull. Soc. Chim. Fr. 1958, 23 - 21
Zakatov VV.Dubina VL.Torubarov IV. Zh. Org. Chim. 1994, 30: 286 -
22a For the addition of triphenylphosphine to o-quinone-monoimides see:
Heine HW.Empfield JR.Golobish TD. J. Org. Chem. 1986, 51: 829 -
22b For the addition of Wittig-Horner reagents see:
Boulos LS.Arsanious MHN. Phosphorus Sulfur Relat. Elem. 1988, 89: 185 -
22c
Boulos LS.Arsanious MHN. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 36: 23 -
22d For the addition of alkyl phosphites and triphenyl phosphine to azido quinoneimides see:
Khir-el-Din N.Nada NN.Ramla M.Zayeed MP. Synth. Commun. 2002, 32: 603 -
22e For Lawesson’s reagent addition to p-quinonemonoimides see:
Boulos LS.Hennawy IT.Arsanious HN. Heteroat. Chem. 1994, 5: 127 - 23
Adams R.Wankel RA. J. Am. Chem. Soc. 1951, 73: 2219 - 24
Friedrichsen W.Oeser HG. Justus Liebigs Ann. Chem. 1978, 1129 - 25
Adams R.Edwards JD. J. Am. Chem. Soc. 1952, 74: 2603 - 26
Adams R.Walter CR. J. Am. Chem. Soc. 1951, 73: 1152 -
27a
Tichenor MS.Kastrinsky DB.Boger DL. J. Am. Chem. Soc. 2004, 26: 8396 -
27b
Kraus GA.Yue S.Sy J. J.Org. Chem. 1985, 50: 284 - 28
Adams R.Acker DS. J. Am. Chem. Soc. 1952, 74: 2605 -
29a
Adams R.Acker DS. J. Am. Chem. Soc. 1952, 74: 5872 -
29b
Jackson SK.Banfield SC.Kerr MA. Org. Lett. 2005, 7: 1215 - 30
Heine HW.Barchiesi BJ.Williams EA. J. Org. Chem. 1984, 49: 2560 - 31
Heine HW.Williams EA. Recl. Trav. Chim. Pays-Bas 1986, 105: 403 - 32
Heine HW.Suriano JA.Winkel C.Burik A.Taylor CM. J. Org. Chem. 1989, 54: 5926 - 33
Nicolaou KC.Sugita K.Baran PS.Zhong Y.-L. Angew. Chem. Int. Ed. 2001, 40: 207 - 34
Pfundt G.Schenck GO. In 1,4-Cycloaddition ReactionsHamer J. Academic Press; New York: 1967. Chap. 11. -
35a
Mustafa A.Kamel M. Science 1953, 117: 234 -
35b
Mustafa A.Kamel M. J. Am. Chem. Soc. 1953, 75: 2939 -
35c
Mustafa A.Kamel M. J. Am. Chem. Soc. 1955, 77: 5630 -
35d
Mustafa A.Kamel M. J. Org. Chem. 1957, 22: 1053 - 36
Adams R.Moje W. J. Am. Chem. Soc. 1952, 74: 5560 -
37a
Friedrichsen W.Oeser HG. Tetrahedron Lett. 1974, 33: 2827 -
37b
Friedrichsen W.Oeser HG. Tetrahedron Lett. 1974, 33: 4373 -
37c
Friedrichsen W.Oeser HG. Tetrahedron Lett. 1975, 34: 1489 -
37d
Friedrichsen W.Oeser HG. Justus Liebigs Ann. Chem. 1978, 1146 -
37e
Friedrichsen W.Oeser HG. Justus Liebigs Ann. Chem. 1978, 1161 - 38
Friedrichsen W.Betz M.Buldt E.Jurgens HJ.Schmidt R.Visser K. Justus Liebigs Ann. Chem. 1978, 440 - 39
Kanematsu K.Ando I.Yamashita O. J. Am. Chem. Soc. 1977, 99: 871 - 40
Parker KA.Kang S.-K. J. Org. Chem. 1979, 44: 1536 - 41
Mukaiyama T.Sagawa Y.Kobayashi S. Chem. Lett. 1987, 2169 - 42
Boger DL.Zarrinmayeh H. J. Org. Chem. 1990, 55: 1379 -
43a
Boger DL.Coleman RS. J. Am. Chem. Soc. 1988, 110: 1321 -
43b
Boger DL.Coleman RS. J. Am. Chem. Soc. 1988, 110: 4796 - 44
Engler TA.Meduna SP.LaTessa KO.Chai W. J. Org. Chem. 1996, 61: 8598 - 45
Engler TA.Luterman D. J. Org. Chem. 1998, 63: 314 -
46a
Engler TA.Chai W.Lynch KW. Tetrahedron Lett. 1995, 36: 7003 -
46b
Engler TA.Chai W.LaTessa KO. J. Org. Chem. 1996, 61: 9297 -
47a
Engler TA.Chai W.Wanner J. Tetrahedron Lett. 1997, 38: 6135 -
47b
Engler TA.Wanner J. J. Org. Chem. 2000, 65: 2444 -
48a
Engler TA.Scheibe CM. J. Org. Chem. 1998, 63: 6247 -
48b
Engler TA.Chai W. Tetrahedron Lett. 1996, 38: 6969 - 50
Nair V.Dhanya R.Rajesh C.Bhadbhade MM.Manoj K. Org. Lett. 2004, 6: 4743 - 51
Nair V.Rajesh C.Dhanya R.Rath NP. Org. Lett. 2002, 4: 953 - 52
Nair V.Dhanya R.Vidya N.Devipriya S. Synthesis 2005, in press - 53
Friedrichsen W.Schwarz I. Tetrahedron Lett. 1977, 36: 3581 - 54
Nair V.Rajesh C.Dhanya R.Rath NP. Tetrahedron Lett. 2002, 43: 5349 - 55
Nair V.Rajesh C.Vinod AU.Bindu S.Sreekanth AR.Mathen JS.Balagopal L. Acc. Chem. Res. 2003, 36: 899 ; and the references cited therein - 56
Nair V.Dhanya R.Viji S. Tetrahedron 2005, 61: 5843 - 57
Baxter I.Cameron DW. Chem. Ind. 1967, 33: 1403 - 58
Parker KA.Mindt TL. Org. Lett. 2002, 4: 4265
References
Nair, V.; Dhanya, R. unpublished results.