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Angewandte Chemie - International Edition

Volumn 46, Issue 7, 2007, Pages 1168-1171

The exciting chemistry of tetraazidomethane

(5) Banert, Klaus a Joo, Young Hyuk a Rüffer, Tobias a Walfort, Bernhard a Lang, Heinrich a

a CHEMNITZ UNIVERSITY OF TECHNOLOGY (Germany)

Author keywords

Azides; Dipolar cycloaddition; Explosives; Nitrogen heterocycles; Nucleophilic substitution

Indexed keywords

DISSOCIATION; NITROGEN; PHASE TRANSITIONS; REACTION KINETICS;

DIPOLAR CYCLOADDITION; NITROGEN HETEROCYCLES; NUCLEOPHILIC SUBSTITUTION;

AROMATIC POLYMERS;

EID: 34250726055 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/anie.200603960 Document Type: Article

Times cited : (110)

References (48)

1
- 27644470140
- Reviews: a
- Reviews: a) C. Knapp, J. Passmore, Angew. Chem. 2004, 116, 4938- 4941;
- (2004) Angew. Chem , vol.116 , pp. 4938-4941
- Knapp, C.¹ Passmore, J.²

2
- 4744362717
- Angew. Chem. Int. Ed. 2004, 43, 4834- 4836;
- (2004) Chem. Int. Ed , vol.43 , pp. 4834-4836
- Angew¹

3
- 14744293096
- b) H.-J. Himmel, B. Hoge, Nachr. Chem. 2005, 53, 225-235.
- (2005) Nachr. Chem , vol.53 , pp. 225-235
- Himmel, H.-J.¹ Hoge, B.²

4
- 4544236102
- a) T. M. Klapötke, B. Krumm, P. Mayer, I. Schwab, Angew. Chem. 2003, 115, 6024-6026;
- (2003) Angew. Chem , vol.115 , pp. 6024-6026
- Klapötke, T.M.¹ Krumm, B.² Mayer, P.³ Schwab, I.⁴

5
- 0346158949
- Angew. Chem. Int. Ed. 2003, 42, 5843-5846;
- (2003) Chem. Int. Ed , vol.42 , pp. 5843-5846
- Angew¹

6
- 0348241038
- b) R. Haiges, J. A. Boatz, A. Vij, M. Gerken, S. Schneider, T. Schroer, K. O. Christe, Angew. Chem. 2003, 115, 6027-6031;
- (2003) Angew. Chem , vol.115 , pp. 6027-6031
- Haiges, R.¹ Boatz, J.A.² Vij, A.³ Gerken, M.⁴ Schneider, S.⁵ Schroer, T.⁶ Christe, K.O.⁷

7
- 0346158951
- Angew. Chem. Int. Ed. 2003, 42, 5847-5851;
- (2003) Chem. Int. Ed , vol.42 , pp. 5847-5851
- Angew¹

8
- 17044396403
- c) R. Haiges, J. A. Boatz, A. Vij, V. Vij, M. Gerken, S. Schneider, T. Schroer, M. Yousufuddin, K. O. Christe, Angew. Chem. 2004, 116, 6844-6848;
- (2004) Angew. Chem , vol.116 , pp. 6844-6848
- Haiges, R.¹ Boatz, J.A.² Vij, A.³ Vij, V.⁴ Gerken, M.⁵ Schneider, S.⁶ Schroer, T.⁷ Yousufuddin, M.⁸ Christe, K.O.⁹

9
- 10944228046
- Angew. Chem. Int. Ed. 2004, 43, 6676-6680;
- (2004) Chem. Int. Ed , vol.43 , pp. 6676-6680
- Angew¹

10
- 0842349049
- d) R. Haiges, A. Vij, J. A. Boatz, S. Schneider, T. Schroer, M. Gerken, K. O. Christe, Chem. Eur. J. 2004, 10, 508-517;
- (2004) Chem. Eur. J , vol.10 , pp. 508-517
- Haiges, R.¹ Vij, A.² Boatz, J.A.³ Schneider, S.⁴ Schroer, T.⁵ Gerken, M.⁶ Christe, K.O.⁷

11
- 4744340846
- e) R. Haiges, J. A. Boatz, S. Schneider, T. Schroer, M. Yousufuddin, K. O. Christe, Angew. Chem. 2004, 116, 3210-3214;
- (2004) Angew. Chem , vol.116 , pp. 3210-3214
- Haiges, R.¹ Boatz, J.A.² Schneider, S.³ Schroer, T.⁴ Yousufuddin, M.⁵ Christe, K.O.⁶

12
- 4544270653
- Angew. Chem. Int. Ed. 2004, 43, 3148-3152;
- (2004) Chem. Int. Ed , vol.43 , pp. 3148-3152
- Angew¹

13
- 27644487941
- f) R. Haiges, J. A. Boatz, R. Bau, S. Schneider, T. Schroer, M. Yousufuddin, K. O. Christe, Angew. Chem. 2005, 117, 1894-1899;
- (2005) Angew. Chem , vol.117 , pp. 1894-1899
- Haiges, R.¹ Boatz, J.A.² Bau, R.³ Schneider, S.⁴ Schroer, T.⁵ Yousufuddin, M.⁶ Christe, K.O.⁷

14
- 17044409179
- Angew. Chem. Int. Ed. 2005, 44, 1860-1865;
- (2005) Chem. Int. Ed , vol.44 , pp. 1860-1865
- Angew¹

15
- 0002561452
- g) I. C. Tornieporth-Oetting, T. M. Klapötke, Angew. Chem. 1995, 107, 559-568;
- (1995) Angew. Chem , vol.107 , pp. 559-568
- Tornieporth-Oetting, I.C.¹ Klapötke, T.M.²

16
- 33748512545
- Angew. Chem. Int. Ed. Engl. 1995, 34, 511-520;
- (1995) Angew. Chem. Int. Ed. Engl , vol.34 , pp. 511-520

17
- 0000525880
- h) T. M. Klapötke, H. Nöth, T. Schütt, M. Warchhold, Angew. Chem. 2000, 112, 2197-2199;
- (2000) Angew. Chem , vol.112 , pp. 2197-2199
- Klapötke, T.M.¹ Nöth, H.² Schütt, T.³ Warchhold, M.⁴

18
- 0039592927
- Angew. Chem. Int. Ed. 2000, 39, 2108-2109;
- (2000) Chem. Int. Ed , vol.39 , pp. 2108-2109
- Angew¹

19
- 0003753834
- i) A. C. Filippou, P. Portius, D. U. Neumann, K.-D. Wehrstedt, Angew. Chem. 2000, 112, 4524-4527;
- (2000) Angew. Chem , vol.112 , pp. 4524-4527
- Filippou, A.C.¹ Portius, P.² Neumann, D.U.³ Wehrstedt, K.-D.⁴

20
- 0034605921
- Angew. Chem. Int. Ed. 2000, 39, 4333-4336;
- (2000) Chem. Int. Ed , vol.39 , pp. 4333-4336
- Angew¹

21
- 33749041183
- j) M.-J. Crawford, A. Ellern, P. Mayer, Angew. Chem. 2005, 117, 8086-8090;
- (2005) Angew. Chem , vol.117 , pp. 8086-8090
- Crawford, M.-J.¹ Ellern, A.² Mayer, P.³

22
- 29144436717
- Angew. Chem. Int. Ed. 2005, 44, 7874-7878.
- (2005) Chem. Int. Ed , vol.44 , pp. 7874-7878
- Angew¹

23
- 27144439505
- Q. S. Li, H. X. Duan, J. Phys. Chem. A 2005, 109, 9089-9094.
- (2005) J. Phys. Chem. A , vol.109 , pp. 9089-9094
- Li, Q.S.¹ Duan, H.X.²

24
- 0001147897
- A. Hassner, M. Stern, H. E. Gottlieb, F. Frolow, J. Org. Chem. 1990, 55, 2304-2306.
- (1990) J. Org. Chem , vol.55 , pp. 2304-2306
- Hassner, A.¹ Stern, M.² Gottlieb, H.E.³ Frolow, F.⁴

25
- 34250785367
- We prepared triazidomethane from iodoform and a concentrated solution of tributylhexadecylphosphonium azide in chloroform
- We prepared triazidomethane from iodoform and a concentrated solution of tributylhexadecylphosphonium azide in chloroform.

26
- 34250710337
- 3 in chloroform.
- 3 in chloroform.

27
- 34250732023
- H. G. Viehe, Z. Janousek, Ger. Offen., Patent DE 2033276, 1972 [Chem. Abstr. 1972, 76, 85425];
- a) H. G. Viehe, Z. Janousek, Ger. Offen., Patent DE 2033276, 1972 [Chem. Abstr. 1972, 76, 85425];

28
- 0000894880
- b) G. Barany, A. L. Schroll, A. W. Mott, D. A. Halsrud, J. Org. Chem. 1983, 48, 4750-4761;
- (1983) J. Org. Chem , vol.48 , pp. 4750-4761
- Barany, G.¹ Schroll, A.L.² Mott, A.W.³ Halsrud, D.A.⁴

29
- 0030128410
- c) C. Bolln, H. Frey, R. Mülhaupt, Macromolecules 1996, 29, 3111-3116;
- (1996) Macromolecules , vol.29 , pp. 3111-3116
- Bolln, C.¹ Frey, H.² Mülhaupt, R.³

30
- 34250703423
- d) E. E. Gilbert, Tetrahedron 1969, 25, 1801-1806.
- (1969) Tetrahedron , vol.25 , pp. 1801-1806
- Gilbert, E.E.¹

31
- 0003550135
- 2nd ed, Thieme, Stuttgart
- L. F. Tietze, T. Eicher, Reaktionen und Synthesen im organischchemischen Praktikum und Forschungslaboratorium, 2nd ed., Thieme, Stuttgart, 1991, pp. 39-40.
- (1991) Reaktionen und Synthesen im organischchemischen Praktikum und Forschungslaboratorium , pp. 39-40
- Tietze, L.F.¹ Eicher, T.²

32
- 34250699223
- Crystallographic data for 4a: C25H36N 12, M, 504.66, monoclinic, space group P2 1/c, Z, 4, a, 11.1484(6, b, 11.0673(5, c, 21.2600(13) Å, β, 90.153(5)°, V, 2623.1(2) Å3, ρcalcd, 1.278 g cm-3, T, 298 K, crystal size 0.40 x 0.35 x 0.20 mm3, R, 0.0605 (I>2σ(I, Rw, 0.2078, GOF, 1.023. Crystallographic data for 4b: C33H48N12, M, 612.83, triclinic, space group P1, Z, 4, a, 12.250(4, b, 12.373(4, c, 22.192(5) Å, α, 81.041(9, β, 82.336(9, γ, 85.500(11)°, V, 3287.1(18) Å3, ρcalcd, 1.238 g cm-3, T, 298 K, crystal size 0.30 x 0.30 x 0.30 mm3, R, 0.0762 I > 2σ
- 3, R = 0.0762 (I > 2σ(I), Rw = 0.2545, GOF = 1.048. CCDC-619288 and -619287 (4a and 4b, respectively) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.

33
- 34250711050
- Because the yield of 1 could not be determined by weighing (see the Safety Precautions, the integration of the 13C NMR signal (without decoupling, delay of 60 s between the pulses) relative to those of weighed amounts of CCl4, CBr4, and tetrachloroethene was used. This resulted in a yield of 1-2% for the synthesis of 1 from 2h including isolation by gas chromatography and a yield of 60-87% for the generation of 1 from 3a and NaN3 or LiN3 without workup. As the method described above for determination of the yield is very laborious and inaccurate, the yields of the stable succeeding products of 1 (Schemes 1 and 2) were based on precursor 2h. Thus, we obtained 6 in 3% yield (based on 2h) as well as 8 in 2, 9a in 2, 9b in 0.1, 10a in 0.7, and 10b in 0.1% yield
- 3 without workup. As the method described above for determination of the yield is very laborious and inaccurate, the yields of the stable succeeding products of 1 (Schemes 1 and 2) were based on precursor 2h. Thus, we obtained 6 in 3% yield (based on 2h) as well as 8 in 2%, 9a in 2%, 9b in 0.1%, 10a in 0.7%, and 10b in 0.1% yield.

34
- 0002554578
- U. Müller, K. Dehnicke, Angew. Chem. 1966, 78, 825;
- (1966) Angew. Chem , vol.78 , pp. 825
- Müller, U.¹ Dehnicke, K.²

35
- 84904669188
- Angew. Chem. Int. Ed. Engl. 1966, 5, 841-842.
- (1966) Angew. Chem. Int. Ed. Engl , vol.5 , pp. 841-842

36
- 33845262419
- Jan. 17
- R. K. Howe, M. L. Rueppel, Chem. Eng. News 1983, 61 (Jan. 17), 4.
- (1983) Chem. Eng. News , Issue.61 , pp. 4
- Howe, R.K.¹ Rueppel, M.L.²

37
- 33845247254
- April 25
- L. A. Burke, Chem. Eng. News 1983, 61 (April 25), 2.
- (1983) Chem. Eng. News , Issue.61 , pp. 2
- Burke, L.A.¹

38
- 33845246079
- March 5
- a) W. Beck, J. Geisenberger, Chem. Eng. News 1984, 62 (March 5), 39;
- (1984) Chem. Eng. News , Issue.62 , pp. 39
- Beck, W.¹ Geisenberger, J.²

39
- 84943695966
- b) J. Geisenberger, I. Eble, I. Neibrich, U. Nassel, W. Beck, Z. Naturforsch. B 1987, 42, 55-64.
- (1987) Z. Naturforsch. B , vol.42 , pp. 55-64
- Geisenberger, J.¹ Eble, I.² Neibrich, I.³ Nassel, U.⁴ Beck, W.⁵

40
- 0030765588
- and references therein
- M. A. Petrie, J. A. Sheehy, J. A. Boatz, G. Rasul, G. K. S. Prakash, G. A. Olah, K. O. Christe, J. Am. Chem. Soc. 1997, 119, 8802-8808, and references therein.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 8802-8808
- Petrie, M.A.¹ Sheehy, J.A.² Boatz, J.A.³ Rasul, G.⁴ Prakash, G.K.S.⁵ Olah, G.A.⁶ Christe, K.O.⁷

41
- 85171973292
- and references therein
- W. Kesting, Ber. Dtsch. Chem. Ges. B 1924, 57, 1321-1324, and references therein.
- (1924) Ber. Dtsch. Chem. Ges. B , vol.57 , pp. 1321-1324
- Kesting, W.¹

42
- 34250782941
- [18] was not successful. However, variants of this click reaction in water-free solvents have also hitherto failed.
- [18] was not successful. However, variants of this click reaction in water-free solvents have also hitherto failed.

43
- 84867726453
- Review on click reaction azide/alkyne
- Review on click reaction (azide/alkyne): V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51-68.
- (2006) Eur. J. Org. Chem , pp. 51-68
- Bock, V.D.¹ Hiemstra, H.² van Maarseveen, J.H.³

44
- 34250708209
- 3 and concentrated aqueous hydrochloric acid (59% yield over the two steps).
- 3 and concentrated aqueous hydrochloric acid (59% yield over the two steps).

45
- 37049097001
- D. M. Kanjia, J. Mason, I. A. Stenhouse, R. E. Banks, N. D. Venayak, J. Chem. Soc. Perkin Trans. 2 1981, 975-979.
- (1981) J. Chem. Soc. Perkin Trans. 2 , pp. 975-979
- Kanjia, D.M.¹ Mason, J.² Stenhouse, I.A.³ Banks, R.E.⁴ Venayak, N.D.⁵

46
- 34250751540
- The spectroscopic data for 4a,b, 6, 8, 9a,b, and 10a,b as well as (further) suggestions of reaction mechanisms to explain the formation of 6, 9a,b, and 10a,b are collected in the Supporting Information.
- The spectroscopic data for 4a,b, 6, 8, 9a,b, and 10a,b as well as (further) suggestions of reaction mechanisms to explain the formation of 6, 9a,b, and 10a,b are collected in the Supporting Information.

47
- 0842323372
- a) F. D. Marsh, M. D. Hermes, J. Am. Chem. Soc. 1964, 86, 4506-4507;
- (1964) J. Am. Chem. Soc , vol.86 , pp. 4506-4507
- Marsh, F.D.¹ Hermes, M.D.²

48
- 0010626119
- b) F. D. Marsh, J. Org. Chem. 1972, 37, 2966-2969.
- (1972) J. Org. Chem , vol.37 , pp. 2966-2969
- Marsh, F.D.¹

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