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Synlett 2005(7): 1073-1089
DOI: 10.1055/s-2005-865213
DOI: 10.1055/s-2005-865213
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Planar Dehydro[8]annulenes and Their Ramifications: Substituted Tribenzo[a,c,e]cyclooctenes and Tetrabenzo[a,c,e,g]cyclooctenes
Further Information
Received
4 February 2005
Publication Date:
14 April 2005 (online)
Publication History
Publication Date:
14 April 2005 (online)
Abstract
Our research endeavors on planar dehydro[8]annulenes were broadened into areas concerning syntheses and studies of strategically substituted tribenzo[a,c,e]cyclooctenes and tetrabenzo[a,c,e,g]cyclooctenes. Further conversion of these scaffolds led to novel molecules containing central planar eight-membered ring compounds.
Key words
dehydro[8]annulenes - tribenzo[a,c,e]cyclooctenes - tetrabenzo[a,c,e,g]cyclooctenes
-
1a
Kekulé A. Bull. Soc. Chim. Fr. 1865, 3: 98 -
1b
Kekulé A. Liebigs Ann. Chem. 1866, 137: 129 - 2
Armit JW.Robinson R. J. Chem. Soc. 1925, 127: 1604 -
3a
Hückel E. Z. Phys. 1931, 70: 204 -
3b
Hückel E. Z. Elektrochem. 1937, 43: 752 -
3c
Hückel E. Grundzüge der Theorie ungesättigter und aromatischer Verbindungen Verlag Chemie; Berlin: 1938. -
4a
Willstätter R.Waser E. Ber. 1911, 44: 3423 -
4b
Willstäter R.Heidelberger M. Ber. 1913, 46: 517 -
5a
Raphael RA. In Non-benzenoid Aromatic CompoundsGinsburg D. Interscience; New York: 1959. Chap. VIII. -
5b
Schröder G. Cyclooctatetraen Verlag Chemie; Weinheim: 1965. -
5c
Paquette LA. Tetrahedron 1975, 31: 2855 -
6a
Salem L. The Molecular Orbital Theory of Conjugated Systems Benjamin; New York: 1966. p.486-491 -
6b
Englman R. The Jahn-Teller Effect in Molecules and Crystals Wiley-Interscience; London: 1966. p.243-245 -
7a
Katz TJ. J. Am. Chem. Soc. 1960, 82: 3784 -
7b
Katz TJ. J. Am. Chem. Soc. 1960, 82: 3785 -
8a
Katz TJ.Strauss HL. J. Chem. Phys. 1960, 32: 1873 -
8b
Strauss HL.Katz TJ.Fraenkel GK. J. Am. Chem. Soc. 1963, 85: 2360 -
9a
Olah GA.Staral JS.Paquette LA. J. Am. Chem. Soc. 1976, 98: 1267 -
9b
Olah GA.Staral JS.Liang G.Paquette LA.Melega WP.Carmody MJ. J. Am. Chem. Soc. 1977, 99: 3349 - 10
Wong HNC.Chan KH.Cheung SS. Org. Chem. (Shanghai) 1991, 11: 13 - 11
Dürr H.Klauck G.Peters K.von Schnering HG. Angew. Chem., Int. Ed. Engl. 1983, 22: 332 -
12a
Wong HNC.Garratt PJ.Sondheimer F. J. Am. Chem. Soc. 1974, 96: 5604 -
12b
Wong HNC.Sondheimer F. Tetrahedron 1981, 37 (S1): 99 -
13a
Einstein FWB.Willis AC.Cullen WR.Soulen RL. J. Chem. Soc., Chem. Commun. 1981, 520 -
13b
Button WE.Ferraris JP.Soulen RL. J. Am. Chem. Soc. 1982, 104: 5322 -
13c
Heilbronner E.Wirz J. Helv. Chim. Acta 1984, 67: 47 - 14
Wilcox CF.Farley EN. J. Org. Chem. 1985, 50: 351 - 15
Huang NZ.Sondheimer F. Acc. Chem. Res. 1982, 15: 96 -
16a
Wong HNC.Sondheimer F. Angew. Chem., Int. Ed. Engl. 1976, 15: 117 -
16b
Wong HNC.Chan T.-L.Sondheimer F. Tetrahedron Lett. 1978, 667 -
16c
Wong HNC.Sondheimer F. J. Org. Chem. 1980, 45: 2438 -
16d
Wong HNC.Sondheimer F. Tetrahedron Lett. 1980, 21: 983 -
16e
Huang N.-Z.Jia J.-H.Wang L.-L.Chan T.-L.Mak TCW. Tetrahedron Lett. 1982, 23: 4797 -
16f
Chan T.-L.Huang N.-Z.Sondheimer F. Tetrahedron 1983, 39: 427 -
16g
Chan T.-L.Mak TCW.Poon C.-D.Wong HNC.Jia J.-H.Wang L.-L. Tetrahedron 1986, 42: 655 -
17a
Wong HNC.Sondheimer F.Goodin R.Breslow R. Tetrahedron Lett. 1976, 2715 -
17b
Kojima H.Bard AJ.Wong HNC.Sondheimer F. J. Am. Chem. Soc. 1976, 98: 5560 -
18a
Gerson F.Martin WB.Plattner G.Sondheimer F.Wong HNC. Helv. Chim. Acta 1976, 59: 2038 -
18b
Gerson F.Heckendorn R.Wong HNC. Helv. Chim. Acta 1983, 20: 1815 - 19
Gorter S.de Graaff RAG.Romers C.Sondheimer F.Wong HNC. J. Chem. Soc., Perkin Trans. 2 1981, 478 -
20a
Huang N.-Z.Mak TCW.Li W.-K. Tetrahedron Lett. 1981, 22: 3765 -
20b
Li W.-K.Chiu S.-W.Mak TCW.Huang N.-Z. J. Mol. Struct. (Theochem) 1983, 94: 285 -
20c
Wong HNC.Li W.-K. J. Chem. Res., Synop. 1984, 302 -
21a
Shuttleworth RG.Rapson WS.Stewart ET. J. Chem. Soc. 1944, 71 -
21b
Gugel H.Meier H. Chem. Ber. 1980, 113: 1431 -
22a
Tochtermann W.Timm H. Tetrahedron Lett. 1978, 2145 -
22b
Tochtermann W.Oppenlaender K.Walter U. Chem. Ber. 1964, 97: 1329 - 23
Wong HNC. Ph.D. Thesis University College London; U.K.: 1976. - 24
Huang N.-Z. Chem. Ind. (London) 1980, 364 -
25a
Xing Y.-D.Huang N.-Z. J. Org. Chem. 1982, 47: 140 -
25b
Xing Y.-D.Gong Q.-Q.Huang N.-Z. Acta Chim. Sinica 1983, 41: 934 - 26
Wong HNC. Acc. Chem. Res. 1989, 22: 145 - 27
Hellwinkel D.Reif G. Angew. Chem., Int. Ed. Engl. 1970, 9: 527 - 28
Wong HNC.Hou X.-L. Synthesis 1985, 1111 - 29
Hou X.-L.Wong HNC. J. Am. Chem. Soc. 1987, 109: 1868 - 30
Wang X.-M.Hou X.-L.Zhou Z.-Y.Mak TCW.Wong HNC. J. Org. Chem. 1993, 58: 7498 - 31
Mitchell RH.Weerawarna SA. Tetrahedron Lett. 1986, 27: 463 and references cited therein - 32
Felder P.Gerson F.Gescheidt G.Heckendorn R.Tong TH.Wang X.-M.Wong HNC.Hou X.-L. Helv. Chim. Acta 1991, 74: 644 - 33
Wang X.-M.Wang R.-J.Mak TCW.Wong HNC. J. Am. Chem. Soc. 1990, 112: 779 - For reviews, see:
-
34a
Hünig S.Erk P. Adv. Mater. 1991, 3: 225 -
34b
Panetta CA.Heimer NE.Huseey CL.Metzger RM. Synlett 1991, 301 - 35
Rapson WS.Schuttleworth PG.Niekark JN. J. Chem. Soc. 1943, 326 - For reviews, see:
-
36a
Mak TCW.Wong HNC. Top. Curr. Chem. 1987, 140: 141 -
36b
Mak TCW.Wong HNC. In Comprehensive Supramolecular Chemistry Vol. 6:MacNicol DD.Toda F.Bishop P. Pergamon Press; Oxford: 1996. p.351-369 - 37
Huang N.-Z.Mak TCW. J. Chem. Soc., Chem. Commun. 1982, 543 - 38
Wong HNC.Man Y.-M.Mak TCW. Tetrahedron Lett. 1987, 28: 6359 - 39
Man Y.-M.Mak TCW.Wong HNC. J. Org. Chem. 1990, 55: 3214 -
40a
Keay BA.Plaumann HP.Rajapaksa D.Rodrigo R. Can. J. Chem. 1983, 61: 1987 -
40b
Yang X.-P.Du D.-M.Li Q.Mak TCW.Wong HNC. Chem. Commun. 1999, 1607 -
41a
Gust D.Senkler GH.Mislow K. J. Chem. Soc., Chem. Commun. 1972, 1345 -
41b
Rashi-Ranjbar P.Man Y.-M.Sandström J.Wong HNC. J. Org. Chem. 1989, 54: 4888 -
41c
Rajca A.Safronov A.Rajca S.Wongsriratanakul J. J. Am. Chem. Soc. 2000, 122: 3351 - 42
Wen J.-F. D.Sc. Thesis Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences; P. R. China: 2003. - 43
Wen J.-F.Hong W.Yuan K.Mak TCW.Wong HNC. J. Org. Chem. 2003, 68: 8918 - 44
Hui CW.Mak TCW.Wong HNC. Tetrahedron 2004, 60: 3523 - For examples, see:
-
45a
Kabir SMH.Iyoda M. Synthesis 2000, 1839 -
45b
Rajca A.Wang H.Bolshov P.Rajca S. Tetrahedron 2001, 57: 3725 -
45c
Kabir SMH.Hasegawa M.Kuwatani Y.Yoshia M.Matsuyama H.Iyoda M. J. Chem. Soc., Perkin Trans. 1 2001, 159 - 46
Wittig G.Klar G. Liebigs Ann. Chem. 1967, 704: 91 - 47
Lai C.-W.Lam C.-K.Lee H.-K.Mak TCW.Wong HNC. Org. Lett. 2003, 5: 823