References and Notes
1a
Narita M.
Pittman CU.
Synthesis
1976,
489
1b
Kreif A.
Tetrahedron
1986,
42:
1204
1c
TTF Chemistry
Yamada J.-i.
Sugimoto T.
Springer;
Heidelberg:
2004.
1d
Otsubo T.
Takimiya K.
Bull. Chem. Soc. Jpn.
2004,
77:
43
2a
Pease AR.
Jeppesen JO.
Stoddart JF.
Luo Y.
Collier CP.
Heath JR.
Acc. Chem. Res.
2001,
34:
433
2b
Becher J.
Jeppesen JO.
Nielsen K.
Synth. Met.
2003,
133-134:
309
3
Wudl F.
Smith G.
Hafnagel EJ.
J. Chem. Soc. D
1970,
1453
4
Ferraris J.
Cowan DO.
Walatka VV.
Perlstein JH.
J. Am. Chem. Soc.
1973,
95:
948
5
Acker DS.
Hertler WR.
J. Am. Chem. Soc.
1962,
84:
3370
6
Williams JM.
Beno MA.
Wang HH.
Leung PCW.
Emge TJ.
Geiser U.
Carlson KD.
Acc. Chem. Res.
1985,
18:
261
7
Asmus K.-D.
Acc. Chem. Res.
1979,
12:
436
8
Wudl F.
Srdanov G.
Rosenau B.
Wellman D.
Williams K.
Cox SD.
J. Am. Chem. Soc.
1988,
110:
1316
9
Suzuki T.
Sakimura T.
Tanaka S.
Yamashita Y.
Shiohara H.
Miyashi T.
J. Chem. Soc., Chem. Commun.
1994,
1431
10
Iwasaki F.
Toyoda N.
Akaishi R.
Fujihara H.
Furukawa N.
Bull. Chem. Soc. Jpn.
1988,
61:
2563
11
Sakimura T.
Master Thesis
Tohoku University, Japan:
1990.
12
Otsubo T.
Aso Y.
Takimiya K.
Bull. Chem. Soc. Jpn.
2001,
74:
1789
13
Abarca B.
Asensio G.
Ballesteros R.
Varea T.
J. Org. Chem.
1991,
56:
3224
14
Kurata H.
Monden M.
Kawase T.
Oda M.
Tetrahedron Lett.
1998,
39:
7135
15
Kawase T.
Muro S.
Kurata H.
Oda M.
J. Chem. Soc., Chem. Commun.
1992,
778
16a
Kawase T.
Ueno N.
Oda M.
Tetrahedron Lett.
1992,
33:
5405
16b
Kurata H.
Inase M.
Oda M.
Chem. Lett.
1999,
519
17 Isolation and molecular structure of tri(2-thienyl)methylium were reported: Varea T.
Medio-Simón M.
Abarca B.
Ballesteros R.
Asensio G.
García-Granda S.
Pérez-Carreño E.
Gómez-Beltrán F.
J. Chem. Soc., Chem. Commun.
1993,
1476 ; see also ref. 13
18
Suzuki T.
Shiohara H.
Monobe M.
Sakimura T.
Tanaka S.
Yamashita Y.
Miyashi T.
Angew. Chem., Int. Ed. Engl.
1992,
31:
455
19
Bock H.
Ruppert K.
Merzweiler K.
Fenske D.
Goesmann H.
Angew. Chem., Int. Ed. Engl.
1989,
28:
1684
20
Shiohara H.
Master Thesis
Tohoku University, Japan:
1992.
21
Yamanaka K.
Fujitsuka M.
Ito O.
Aoshima T.
Fukushima T.
Miyashi T.
Bull. Chem. Soc. Jpn.
2003,
76:
1341
22
Aoshima T.
Master Thesis
Tohoku University, Japan:
2000.
23a
Lammertsma K.
Barzaghi M.
Olah GA.
Pople JA.
Kos AJ.
von R. Schleyer P.
J. Am. Chem. Soc.
1983,
105:
5252
23b
Frenking G.
J. Am. Chem. Soc.
1991,
113:
2476
24 X-ray analysis on the dication salt of tetrakis(4-methoxy-phenyl)ethylene showed the twisting angle of 62° for the mixed counter-anion salt containing SbCl6
- and Cl- (ref. 25). PM3 calculation of tetrakis(4-dimethylaminophenyl)eth-ylene predicted twisting of 80.6° for the dication (ref. 26).
25
Rathore R.
Lindeman SV.
Kumar AS.
Kochi JK.
J. Am. Chem. Soc.
1998,
120:
6931
26
Hünig S.
Kemmer M.
Wenner H.
Barbosa F.
Gescheidt G.
Perepichka IG.
Bäuerle P.
Emge A.
Peters K.
Chem. Eur. J.
2000,
6:
2618
27
Malandra JL.
Mills NS.
Kadlecek DE.
Lowery JA.
J. Am. Chem. Soc.
1994,
116:
11622
28
Bock H.
Rauschenbach A.
Ruppert K.
Havlas Z.
Angew. Chem., Int. Ed. Engl.
1991,
30:
714
29a
Horner M.
Hünig S.
J. Am. Chem. Soc.
1977,
99:
6122
29b
Horner M.
Hünig S.
Liebigs Ann. Chem.
1983,
69
29c
Hesse K.
Hünig S.
Liebigs Ann. Chem.
1985,
740
30
Freund W.
Hünig S.
Helv. Chim. Acta
1987,
70:
929
31
Freund W.
Hünig S.
J. Org. Chem.
1987,
52:
2154
32
Hünig S.
Briehn CA.
Bäuerle P.
Emge A.
Chem. Eur. J.
2001,
7:
2745
33a
Musker WK.
Acc. Chem. Res.
1980,
13:
200
33b
Furukawa N.
Bull. Chem. Soc. Jpn.
1997,
70:
2571
34
Alder RW.
Sessions RB.
J. Am. Chem. Soc.
1979,
101:
3651
35
Suzuki T.
Kondo M.
Nakamura T.
Fukushima T.
Miyashi T.
J. Chem. Soc., Chem. Commun.
1997,
2325
36
Suzuki T.
Higuchi H.
Tsuji T.
Nishida J.
Yamashita Y.
Miyashi T. In Chemistry of Nanomolecular Systems
Nakamura T.
Matsumoto T.
Tada H.
Sugiura K.
Springer;
Berlin:
2003.
Chap. 1.
p.3-24
37
Suzuki T.
Nishida J.
Tsuji T.
Angew. Chem., Int. Ed. Engl.
1997,
36:
1329
38
Monk PMS.
Mortimer RJ.
Rosseinsky DR. In Electrochromism: Fundamentals and Applications
VCH;
Weinheim:
1995.
39
McBride JM.
Tetrahedron
1974,
30:
2009
Reviews:
40a
Toda F.
Eur. J. Org. Chem.
2000,
1377
40b
Komarov IV.
Russ. Chem. Rev. (Engl. Transl.)
2001,
70:
991
41
Hounshell WD.
Dougherty DA.
Hummel JP.
Mislow K.
J. Am. Chem. Soc.
1977,
99:
1916
42
Wittig G.
Petri H.
Justus Liebigs Ann. Chem.
1933,
505:
17
43
Maslak P.
Narvaez JN.
Vallombroso TM.
J. Am. Chem. Soc.
1995,
117:
12373
44
Muthyala R. In Chemistry and Application of Leuco Dyes
Plenum Press;
New York:
1997.
45a Reactions of dilithiobiphenyl and diarylketone are very convenient to obtain the diols since the parent biphenyl can be directly converted into dilithiobiphenyl by treatment with n-BuLi/TMEDA: Neugebauer N.
Kos AJ.
von R. Schleyer P.
J. Organomet. Chem.
1982,
228:
107
45b Years later another procedure starting from diphenoic acid dimethyl ester and aryllithium was also reported: Caery KA.
Clegg W.
Elsegood MRJ.
Golding BT.
Hill MNS.
Maskill H.
J. Chem. Soc., Perkin Trans. 1
2002,
2673
46
Suzuki T.
Nishida J.
Tsuji T.
Chem. Commun.
1998,
2193
47 By incorporation of two different diarylmethylium chromophores the reduction of dication 9 proceeds stepwise, thus allowing generation and detection of the bond-dissociated cation radical by steady-state spectroscopy (ref. 46).
48
Hünig S.
Kemmer M.
Wenner H.
Perepichka IF.
Bäuerle P.
Emge A.
Gesheid G.
Chem. Eur. J.
1999,
5:
1969
49a
Zahn S.
Canary JW.
Science
2000,
288:
1404
49b
Zahn S.
Canary JW.
J. Am. Chem. Soc.
2002,
124:
9204
49c
Goto H.
Yashima E.
J. Am. Chem. Soc.
2002,
124:
7943
49d
Suzuki T.
Nishida J.
Hirota E.
Ohkita M.
Tsuji T.
Synth. Met.
2003,
133-134:
357
50a
Westermeier C.
Gallmeier H.-C.
Komma M.
Daub J.
Chem. Commun.
1999,
2427
50b
Beer G.
Niederalt C.
Grimme S.
Daub J.
Angew. Chem. Int. Ed.
2000,
39:
3252
50c
Zelikovich L.
Libman J.
Shanzer A.
Nature
1995,
374:
790
51a
Nishida J.
Suzuki T.
Ohkita M.
Tsuji TJ.
Angew. Chem. Int. Ed.
2001,
40:
3251
51b
Suzuki T.
Yamamoto R.
Higuchi H.
Hirota E.
Ohkita M.
Tsuji T.
J. Chem. Soc., Perkin Trans. 2
2002,
1937
Chiral redox systems based on 1,1"-binaphthyl skeletons have been reported:
52a
Rajca A.
Safronov A.
Rajca S.
Ross CR.
Stezowski JJ.
J. Am. Chem. Soc.
1996,
118:
7272
52b
Gómez R.
Segura JL.
Martín N.
J. Org. Chem.
2000,
65:
7566
52c
Zhou Y.
Zhang D.
Zhu L.
Shuai Z.
Zhu D.
J. Org. Chem.
2006,
71:
2123
53 The binaphthylic dication with 4-Me2NC6H5 groups was also prepared which gave [5]helicene-type donor upon reduction. Further studies were carried out for xanthene and thioxanthene derivatives 10a,b/10a,b
2+ because difficulties were encountered when conducting their optical resolution.
54
Berova N.
Nakanishi K.
Woody RW. In Circular Dichroism: Principles and Applications
2nd ed.;
Wiley-VCH: New York:
2000.
Chiral chemosensors with a helical structure also afford strong CD signaling through geometrical changes upon diastereoselective complexation:
55a
Katoono R.
Kawai H.
Fujiwara K.
Suzuki T.
Chem. Commun.
2005,
5154
55b
Katoono R.
Kawai H.
Fujiwara K.
Suzuki T.
Tetrahedron Lett.
2006,
47:
1513
56
Suzuki T.
Tanaka S.
Higuchi H.
Kawai H.
Fujiwara K.
Tetrahedron Lett.
2004,
45:
8563
57
Michaelis J.
Hettich C.
Mlynek J.
Sandoghdar V.
Nature
2000,
405:
325
58
Rurack K.
Resch-Genger U.
Chem. Soc. Rev.
2002,
31:
116
59
Huber C.
Fähnrich K.
Krause C.
Werner T.
J. Photochem. Photobiol., A
1999,
128:
111
60
Suzuki T.
Migita A.
Higuchi H.
Kawai H.
Fujiwara K.
Tsuji T.
Tetrahedron Lett.
2003,
44:
6837
61
Quinto M.
Bard AJ.
J. Electroanal. Chem.
2001,
498:
67
62
Higuchi H.
Ichioka K.
Kawai H.
Fujiwara K.
Ohkita M.
Tsuji T.
Suzuki T.
Tetrahedron Lett.
2004,
45:
3027
63a
Mizutani T.
Sakai N.
Yagi S.
Takagishi T.
Kitagawa S.
Ogoshi H.
J. Am. Chem. Soc.
2000,
122:
748
63b
Ohmori K.
Kitamura M.
Suzuki K.
Angew. Chem. Int. Ed.
1999,
38:
1226
63c
Kwit M.
Rychlewska U.
Gawrónski J.
New J. Chem.
2002,
26:
1714
63d
Saudan LA.
Bernardinelli G.
Kündig EP.
Synlett
2000,
483
63e
Superchi S.
Casarini D.
Laurita A.
Bavoso A.
Rosini C.
Angew. Chem. Int. Ed.
2001,
40:
451
63f
Mazaleyrat J.-P.
Wright K.
Gaucher A.
Toulemonde N.
Dutot L.
Wakselman M.
Broxterman QB.
Kaptein B.
Oancea S.
Peggion C.
Crisma M.
Formaggio F.
Toniolo C.
Chem. Eur. J.
2005,
11:
6921
64
Ohta K.
Master Thesis
Hokkaido University, Japan:
2006.
65a
Nehira T.
Parish CA.
Jochusch S.
Turro NJ.
Nakanishi K.
Berova N.
J. Am. Chem. Soc.
1999,
121:
8681
65b
Nehira T.
Tanaka K.
Takakuwa T.
Ohshima C.
Masago H.
Pescitelli G.
Wada A.
Berova N.
Appl. Spectrosc.
2005,
59:
121
66 Suzuki, T.; Ohta, K.; Nehira, T.; Kawai, H.; Fujiwara, K. Abstracts of Papers, 18th Symposium on Fundamental Organic Chemistry, Oct. 7-9, 2006, Fukuoka.
67
Suzuki T.
Tanaka S.
Kawai H.
Fujiwara K.
Chem. Asian J.
2007,
2:
171
68
Suzuki T.
Nishida J.
Ohkita M.
Tsuji T.
Angew. Chem. Int. Ed.
2000,
39:
1804
69a
Kawai H.
Takeda T.
Fujiwara K.
Suzuki T.
Tetrahedron Lett.
2004,
45:
8289
69b
Kawai H.
Takeda T.
Fujiwara K.
Inabe T.
Suzuki T.
Cryst. Growth Des.
2005,
5:
2256
69c
Kawai H.
Takeda T.
Fujiwara K.
Suzuki T.
J. Am. Chem. Soc.
2005,
127:
12172
70a
Baldridge KK.
Battersby TR.
Vernon Clark R.
Siegel JS.
J. Am. Chem. Soc.
1997,
119:
7048
70b
Ósawa S.
Sakai M.
Ósawa E.
J. Phys. Chem. A
1997,
101:
1378
70c
Kammermeier S.
Jones PG.
Herges R.
Angew. Chem., Int. Ed. Engl.
1997,
36:
1757
70d
Kaupp G.
Boy J.
Angew. Chem., Int. Ed. Engl.
1997,
36:
48
70e
Suzuki T.
Ono K.
Nishida J.
Takahashi H.
Tsuji T.
J. Org. Chem.
2000,
65:
4944
70f
Suzuki T.
Ono K.
Kawai H.
Tsuji T.
J. Chem. Soc., Perkin Trans. 2
2001,
1798
71a
Toda F.
Tanaka K.
Stein Z.
Goldberg I.
Acta Crystallogr., Sect. C
1996,
52:
177
71b
Baldridge KK.
Kasahara Y.
Ogawa K.
Siegel JS.
Tanaka K.
Toda F.
J. Am. Chem. Soc.
1998,
120:
6167
71c
Toda F.
Tanaka K.
Watanabe M.
Tamura K.
Miyahara I.
Nakai T.
Hirotsu K.
J. Org. Chem.
1999,
64:
3102
71d
Tanaka K.
Takamoto N.
Tezuka Y.
Kato M.
Toda F.
Tetrahedron
2001,
57:
3761
72 Kawai, H.; Takeda, T.; Fujiwara, K.; Suzuki, T. Abstracts of Papers, 18th Symposium on Fundamental Organic Chemistry, Oct. 7-9, 2006, Fukuoka.
73a
Kirchen RP.
Sorensen TS.
J. Am. Chem. Soc.
1978,
100:
6761
73b
McMurry JE.
Hodge CN.
J. Am. Chem. Soc.
1984,
106:
6450
73c
Sorensen TS.
Whitworth SM.
J. Am. Chem. Soc.
1990,
112:
8135
73d
McMurry JE.
Lectka T.
Acc. Chem. Res.
1992,
25:
47
73e
Taeschler C.
Parvez M.
Sorensen TS.
J. Phys. Org. Chem.
2002,
15:
36
74a
Reiter SA.
Nogai SD.
Karaghiosoff K.
Schmidbaur H.
J. Am. Chem. Soc.
2004,
126:
15833
74b
Katz HE.
J. Am. Chem. Soc.
1985,
107:
1420
74c
Hoefelmeyer JD.
Schulte M.
Tschinkl M.
Gabbaï FP.
Coord. Chem. Rev.
2002,
235:
93
74d
Staab HA.
Saupe T.
Angew. Chem., Int. Ed. Engl.
1988,
27:
865
74e
Panisch R.
Bolte M.
Müller T.
J. Am. Chem. Soc.
2006,
128:
9676
75a
Neunteufel RA.
Arnold DR.
J. Am. Chem. Soc.
1973,
95:
4080
75b
Farid S.
Shealer SE.
J. Chem. Soc., Chem. Commun.
1973,
677
75c
Mayer R.
Kröber K.
J. Prakt. Chem.
1974,
316:
907
76a
Asamuma T.
Yamamoto M.
Nishijima Y.
J. Chem. Soc., Chem. Commun.
1975,
56
76b
Mattes SL.
Farid S.
J. Am. Chem. Soc.
1983,
105:
1386
76c
Miyashi T.
Ikeda H.
Takahashi Y.
Acc. Chem. Res.
1999,
32:
815
77a
Schöberl U.
Salbech J.
Daub J.
Adv. Mater. (Weinheim, Ger.)
1992,
4:
41
77b
Ohta A.
Yamashita Y.
J. Chem. Soc., Chem. Commun.
1995,
1761
77c
Lorcy D.
Carlier R.
Robert A.
Tallec A.
Le Maguerés P.
Ouahav L.
J. Org. Chem.
1995,
60:
2443
77d
Benahmed-Gasmi A.
Frère P.
Roncali J.
Elandaloussi E.
Ordun J.
Garin J.
Jubault M.
Gorgues A.
Tetrahedron Lett.
1995,
36:
2983
77e
Hapiot P.
Lorcy D.
Tallec A.
Carlier R.
Robert A.
J. Phys. Chem.
1996,
100:
14823
77f
Moore AJ.
Bryce MR.
Skabara PJ.
Datsanov AS.
Goldenberg LM.
Howard JAK.
J. Chem. Soc., Perkin 1
1997,
3443
77g
Hascoat P.
Lorcy D.
Robert A.
Carlier R.
Tallec A.
Boubekeur K.
Batail P.
J. Org. Chem.
1997,
62:
6086
77h
Yamashita Y.
Tomura M.
Zaman MB.
Imaeda K.
Chem. Commun.
1998,
1657
78
Suzuki T.
Higuchi H.
Ohkita M.
Tsuji T.
Chem. Commun.
2000,
1574
79
Higuchi H.
Ohta E.
Kawai H.
Fujiwara K.
Tsuji T.
Suzuki T.
J. Org. Chem.
2003,
68:
6605
80
Quinkert G.
Wiersdorff W.-W.
Finke M.
Opitz K.
von der Haar F.-G.
Chem. Ber.
1968,
101:
2302
81
Iwashita S.
Ohta E.
Higuchi H.
Kawai H.
Fujiwara K.
Ono K.
Takenaka M.
Suzuki T.
Chem. Commun.
2004,
2076
82
Ohta E.
Higuchi H.
Kawai H.
Fujiwara K.
Suzuki T.
Org. Biomol. Chem.
2005,
3:
3024
83 Ohta, E.; Kawai, H.; Fujiwara, K.; Suzuki, T. Abstracts of Papers, 18th Symposium on Fundamental Organic Chemistry, Oct. 7-9, 2006, Fukuoka.
Similar hydrolytic conversions into quinonemethides were reported for some sterically hindered diarylmethyliums:
84a
Markies PR.
Villena A.
Akkerman OS.
Bickelhaupt F.
Smeets WJJ.
Spek AL.
J. Organomet. Chem.
1993,
463:
7
84b
Barker CC.
Hallas G.
Proc. Chem. Soc., London
1961,
2642
84c
Kawai T.
Nagasu T.
Takeda T.
Fujiwara K.
Tsuji T.
Ohkita M.
Nishida J.
Suzuki T.
Tetrahedron Lett.
2004,
45:
4553
85 Higuchi, H.; Kawai, H.; Fujiwara, K.; Suzuki, T. Abstracts of Papers, Pacifichem, Dec 15-20, 2005, Honolulu, 906.
86
Suzuki T.
Yoshino T.
Ohkita M.
Tsuji T.
J. Chem. Soc., Perkin Trans. 1
2000,
3417
