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Volumn 50, Issue 71, 2014, Pages 10291-10294

Oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′- diamines (BINAMs) via C-C bond cleavage and nitrogen migration: A versatile synthesis of U-shaped azaacenes

(3) Takeda, Youhei a Okazaki, Masato a Minakata, Satoshi a

a OSAKA UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHALENE 2,2' DIAMINE; 1,1' BINAPHTHYL DERIVATIVE; DIAMINE DERIVATIVE; HETEROCYCLIC COMPOUND; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CRYSTAL STRUCTURE; OXIDATION; PHYSICAL CHEMISTRY; QUANTUM YIELD; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84905734505 PISSN: 13597345 EISSN: 1364548X Source Type: Journal
DOI: 10.1039/c4cc04911j Document Type: Article

Times cited : (49)

References (45)

1
- 67650493441
- U. H. F. Bunz Chem.-Eur. J. 2009 15 6780
- (2009) Chem.-Eur. J. , vol.15 , pp. 6780
- Bunz, U.H.F.¹

2
- 79959802180
- G. J. Richards J. P. Hill T. Mori K. Ariga Org. Biomol. Chem. 2011 9 5005
- (2011) Org. Biomol. Chem. , vol.9 , pp. 5005
- Richards, G.J.¹ Hill, J.P.² Mori, T.³ Ariga, K.⁴

3
- 84856597248
- Q. Miao Synlett 2012 326
- (2012) Synlett , pp. 326
- Miao, Q.¹

4
- 84875757606
- U. H. F. Bunz J. U. Engelhart B. D. Lindner M. Schaffroth Angew. Chem., Int. Ed. 2013 52 3810
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 3810
- Bunz, U.H.F.¹ Engelhart, J.U.² Lindner, B.D.³ Schaffroth, M.⁴

5
- 33846970581
- M. Winkler K. N. Houk J. Am. Chem. Soc. 2007 129 1805
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 1805
- Winkler, M.¹ Houk, K.N.²

6
- 83055164372
- K. E. Maly Cryst. Growth Des. 2011 11 5628
- (2011) Cryst. Growth Des. , vol.11 , pp. 5628
- Maly, K.E.¹

7
- 84865227633
- S. More R. Bhosale S. Choudhary A. Mateo-Alonso Org. Lett. 2012 14 4170
- (2012) Org. Lett. , vol.14 , pp. 4170
- More, S.¹ Bhosale, R.² Choudhary, S.³ Mateo-Alonso, A.⁴

8
- 77749292822
- A. Mateo-Alonso N. Kulisic G. Valenti M. Marcaccio F. Paolucci M. Prato Chem.-Asian J. 2010 5 482
- (2010) Chem.-Asian J. , vol.5 , pp. 482
- Mateo-Alonso, A.¹ Kulisic, N.² Valenti, G.³ Marcaccio, M.⁴ Paolucci, F.⁵ Prato, M.⁶

9
- 84880251787
- A. L. Appleton S. M. Brombosz S. Barlow J. S. Sears J.-L. Bredas S. R. Marder U. H. F. Bunz Nat. Commun. 2010 1 91
- (2010) Nat. Commun. , vol.1 , pp. 91
- Appleton, A.L.¹ Brombosz, S.M.² Barlow, S.³ Sears, J.S.⁴ Bredas, J.-L.⁵ Marder, S.R.⁶ Bunz, U.H.F.⁷

10
- 46049101238
- B. Gao M. Wang Y. Cheng L. Wang X. Jing F. Wang J. Am. Chem. Soc. 2008 130 8297
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 8297
- Gao, B.¹ Wang, M.² Cheng, Y.³ Wang, L.⁴ Jing, X.⁵ Wang, F.⁶

11
- 34748904896
- Y. Fogel M. Kastler Z. Wang D. Andrienko G. J. Bodwell K. Müllen J. Am. Chem. Soc. 2007 129 11743
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 11743
- Fogel, Y.¹ Kastler, M.² Wang, Z.³ Andrienko, D.⁴ Bodwell, G.J.⁵ Müllen, K.⁶

12
- 79953250245
- O. Tverskoy F. Rominger A. Peters H.-J. Himmel U. H. F. Bunz Angew. Chem., Int. Ed. 2011 50 3557
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 3557
- Tverskoy, O.¹ Rominger, F.² Peters, A.³ Himmel, H.-J.⁴ Bunz, U.H.F.⁵

13
- 80052453395
- B. D. Lindner J. U. Engelhart O. Tverskoy A. L. Appleton F. Rominger A. Peters H.-J. Himmel U. H. F. Bunz Angew. Chem., Int. Ed. 2011 50 8588
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 8588
- Lindner, B.D.¹ Engelhart, J.U.² Tverskoy, O.³ Appleton, A.L.⁴ Rominger, F.⁵ Peters, A.⁶ Himmel, H.-J.⁷ Bunz, U.H.F.⁸

14
- 84858165564
- M. Akita S. Hiroto H. Shinokubo Angew. Chem., Int. Ed. 2012 51 2894
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 2894
- Akita, M.¹ Hiroto, S.² Shinokubo, H.³

15
- 84867043687
- K. Goto R. Yamaguchi S. Hiroto H. Ueno T. Kawai H. Shinokubo Angew. Chem., Int. Ed. 2012 51 10333
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 10333
- Goto, K.¹ Yamaguchi, R.² Hiroto, S.³ Ueno, H.⁴ Kawai, T.⁵ Shinokubo, H.⁶

16
- 84894129729
- H. Yokoi N. Wachi S. Hiroto H. Shinokubo Chem. Commun. 2013 50 2715
- (2013) Chem. Commun. , vol.50 , pp. 2715
- Yokoi, H.¹ Wachi, N.² Hiroto, S.³ Shinokubo, H.⁴

17
- 33751156391
- Y. Kosugi K. Itoho H. Okazaki T. Yanai J. Org. Chem. 1995 60 5690
- (1995) J. Org. Chem. , vol.60 , pp. 5690
- Kosugi, Y.¹ Itoho, K.² Okazaki, H.³ Yanai, T.⁴

18
- 68949177278
- S. Minakata Acc. Chem. Res. 2009 42 1172
- (2009) Acc. Chem. Res. , vol.42 , pp. 1172
- Minakata, S.¹

19
- 84864403755
- Y. Takeda S. Okumura S. Minakata Angew. Chem., Int. Ed. 2012 51 7804
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 7804
- Takeda, Y.¹ Okumura, S.² Minakata, S.³

20
- 84876049492
- Y. Takeda S. Okumura S. Minakata Synthesis 2013 1029
- (2013) Synthesis , pp. 1029
- Takeda, Y.¹ Okumura, S.² Minakata, S.³

21
- 84884343123
- S. Okumura Y. Takeda K. Kiyokawa S. Minakata Chem. Commun. 2013 49 9266
- (2013) Chem. Commun. , vol.49 , pp. 9266
- Okumura, S.¹ Takeda, Y.² Kiyokawa, K.³ Minakata, S.⁴

22
- 84890147589
- S. Okumura C.-H. Lin Y. Takeda S. Minakata J. Org. Chem. 2013 78 12090
- (2013) J. Org. Chem. , vol.78 , pp. 12090
- Okumura, S.¹ Lin, C.-H.² Takeda, Y.³ Minakata, S.⁴

23
- 0021755806
- Production of benzo[c]cinnoline derivatives through dehydrogenation of biaryldiamines have been reported, see
- D. D. Tanner G. C. Gidley N. Das J. E. Rowe A. Potter J. Am. Chem. Soc. 1984 106 5261
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 5261
- Tanner, D.D.¹ Gidley, G.C.² Das, N.³ Rowe, J.E.⁴ Potter, A.⁵

24
- 0002548430
- J. F. Corbett P. F. Holt J. Chem. Soc. 1961 3695
- (1961) J. Chem. Soc. , pp. 3695
- Corbett, J.F.¹ Holt, P.F.²

25
- 0001414066
- I. Bhatnagar M. V. George J. Org. Chem. 1968 33 2407
- (1968) J. Org. Chem. , vol.33 , pp. 2407
- Bhatnagar, I.¹ George, M.V.²

26
- 79952899091
- Production of carbazoles from biaryldiamines under oxidative or acidic conditions have been reported, see
- L. Racané H. Čičak Z. Mihalić G. Karminski-Zamola V. Tralić-Kulenović Tetrahedron 2011 67 2760
- (2011) Tetrahedron , vol.67 , pp. 2760
- Racané, L.¹ Čičak, H.² Mihalić, Z.³ Karminski-Zamola, G.⁴ Tralić-Kulenović, V.⁵

27
- 37049091456
- J. Cornforth D. D. Ridley A. F. Sierakowski D. Uguen T. W. Wallace J. Chem. Soc., Perkin Trans. 1 1982 2317
- (1982) J. Chem. Soc., Perkin Trans. 1 , pp. 2317
- Cornforth, J.¹ Ridley, D.D.² Sierakowski, A.F.³ Uguen, D.⁴ Wallace, T.W.⁵

28
- 0000737695
- T. Yamato C. Hideshima K. Suehiro M. Tashiro G. K. S. Prakash G. A. Olah J. Org. Chem. 1991 56 6248
- (1991) J. Org. Chem. , vol.56 , pp. 6248
- Yamato, T.¹ Hideshima, C.² Suehiro, K.³ Tashiro, M.⁴ Prakash, G.K.S.⁵ Olah, G.A.⁶

29
- 80053594625
- B.-Y. Lim M.-K. Choi C.-G. Cho Tetrahedron Lett. 2011 52 6015
- (2011) Tetrahedron Lett. , vol.52 , pp. 6015
- Lim, B.-Y.¹ Choi, M.-K.² Cho, C.-G.³

30
- 0037434748
- For reviews on C-C bond activation by transition metal complexes, see
- A. A. Zavitsas J. Phys. Chem. A 2003 107 897
- (2003) J. Phys. Chem. A , vol.107 , pp. 897
- Zavitsas, A.A.¹

31
- 0033119285
- B. Rybtchinski D. Milstein Angew. Chem., Int. Ed. 1999 38 870
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 870
- Rybtchinski, B.¹ Milstein, D.²

32
- 11844273927
- C.-H. Jun Chem. Soc. Rev. 2004 33 610
- (2004) Chem. Soc. Rev. , vol.33 , pp. 610
- Jun, C.-H.¹

33
- 78649977641
- S. M. Bonesi M. Fagnoni Chem.-Eur. J. 2010 16 13572
- (2010) Chem.-Eur. J. , vol.16 , pp. 13572
- Bonesi, S.M.¹ Fagnoni, M.²

34
- 0003412412
- The loss of aromatic resonance energies for naphthalene is 11 kcal/mol smaller than that for benzene:, Wiley-Interscience, New York, 5th edn, Naphthoazirines are transiently formed from the naphthylnitrenes through the photoirradiation and thermal decomposition of naphthylazides
- The loss of aromatic resonance energies for naphthalene is 11 kcal/mol smaller than that for benzene: M. B. Smith and J. March, March's Advanced Organic Chemistry: Reactions, Mechanism, and Structure, Wiley-Interscience, New York, 5th edn, 2001
- (2001) March's Advanced Organic Chemistry: Reactions, Mechanism, and Structure
- Smith, M.B.¹ March, J.²

35
- 0345828873
- A. Maltsev T. Bally M.-L. Tsao M. S. Platz A. Kuhn M. Vosswinkel C. Wentrup J. Am. Chem. Soc. 2003 126 237
- (2003) J. Am. Chem. Soc. , vol.126 , pp. 237
- Maltsev, A.¹ Bally, T.² Tsao, M.-L.³ Platz, M.S.⁴ Kuhn, A.⁵ Vosswinkel, M.⁶ Wentrup, C.⁷

36
- 33749845590
- Nevertheless, neither photoirradiation and thermal decomposition of 2′-azido-[1,1′-binaphthalen]-2-amine (10) nor 2,2′-diazido-1, 1′-binaphthalene (11) gave 2a, indicating that the generation of free-nitrene species in the formation of B would not likely be involved. For the detailed experimental information, see the ESI Naphthoazirines are trapped by various nucleophiles like alcohols and amines, see
- N. P. Gritsan M. S. Platz Chem. Rev. 2006 106 3844
- (2006) Chem. Rev. , vol.106 , pp. 3844
- Gritsan, N.P.¹ Platz, M.S.²

37
- 0002208925
- J. Rigaudy C. Igier J. Barcelo Tetrahedron Lett. 1975 16 3845
- (1975) Tetrahedron Lett. , vol.16 , pp. 3845
- Rigaudy, J.¹ Igier, C.² Barcelo, J.³

38
- 0038095977
- S. E. Carroll B. Nay E. F. V. Scriven H. Suschitzky Tetrahedron Lett. 1977 18 943
- (1977) Tetrahedron Lett. , vol.18 , pp. 943
- Carroll, S.E.¹ Nay, B.² Scriven, E.F.V.³ Suschitzky, H.⁴

39
- 0003134245
- S. E. Carroll B. Nay E. F. V. Scriven H. Suschizky D. R. Thomas Tetrahedron Lett. 1977 36 3175
- (1977) Tetrahedron Lett. , vol.36 , pp. 3175
- Carroll, S.E.¹ Nay, B.² Scriven, E.F.V.³ Suschizky, H.⁴ Thomas, D.R.⁵

40
- 84985523625
- B. Nay E. F. V. Scriven H. Suschitzky Z. U. Khan Synthesis 1977 757
- (1977) Synthesis , pp. 757
- Nay, B.¹ Scriven, E.F.V.² Suschitzky, H.³ Khan, Z.U.⁴

41
- 84917974966
- J. Stieglitz P. N. Leech Chem. Ber. 1913 46 2147
- (1913) Chem. Ber. , vol.46 , pp. 2147
- Stieglitz, J.¹ Leech, P.N.²

42
- 0011673321
- J. Stieglitz P. N. Leech J. Am. Chem. Soc. 1914 36 272
- (1914) J. Am. Chem. Soc. , vol.36 , pp. 272
- Stieglitz, J.¹ Leech, P.N.²

43
- 33645451955
- N. Marion O. Navarro J. Mei E. D. Stevens N. M. Scott S. P. Nolan J. Am. Chem. Soc. 2006 128 4101
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 4101
- Marion, N.¹ Navarro, O.² Mei, J.³ Stevens, E.D.⁴ Scott, N.M.⁵ Nolan, S.P.⁶

44
- 0242299242
- C. J. Tonzola M. M. Alam W. Kaminsky S. A. Jenekhe J. Am. Chem. Soc. 2003 125 13548
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 13548
- Tonzola, C.J.¹ Alam, M.M.² Kaminsky, W.³ Jenekhe, S.A.⁴

45
- 0342971584
- P. E. Burrows Z. Shen V. Bulovic D. M. McCarty S. R. Forrest J. A. Cronin M. E. Thompson J. Appl. Phys. 1996 79 7991
- (1996) J. Appl. Phys. , vol.79 , pp. 7991
- Burrows, P.E.¹ Shen, Z.² Bulovic, V.³ McCarty, D.M.⁴ Forrest, S.R.⁵ Cronin, J.A.⁶ Thompson, M.E.⁷

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