Silicon and germanium azides

Current Organic Chemistry

Volumn 15, Issue 11, 2011, Pages 1700-1719

  Pasinszki, Tibor ^a   Krebsz, Melinda ^a   Wagner, Ödön ^b  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

Applications; Germanium azides; Silicon azides; Spectroscopy; Structure; Synthesis

Indexed keywords

SILICON COMPOUNDS;

AZIDE GROUP; DIPOLAROPHILES; GERMANIA AZIDE; GERMANIUMS (GE); GROUP TRANSFER; ORGANIC SYNTHESIS; ORGANIC TRANSFORMATIONS; SILICON AZIDE; TRANSFER AGENTS; VERSATILE TOOLS;

GERMANIUM COMPOUNDS;

EID: 79958843268     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211795656697     Document Type: Review

References (238)

1. 4. Z. Naturforsch. B 1954, 9b, 500.
2. Thayer, J. S.; West, R. Triphenylazido compounds of group IVA elements. Inorg. Chem., 1964, 3, 406-409.
3. Reichle, W. T. Preparation, properties, and thermal decomposition products of organoazides of silicon, germanium, tin, lead, phosphorus, and sulfur. Inorg. Chem., 1964, 3, 402-406.
4. Moberg, C.; Adolfsson, H. Silyl azides. Science of Synthesis, 2002, 4, 435-449.
5. Peterson, W. R. Jr. Chemistry of organoazidosilanes. Rev. Silicon, Germanium, Tin and Lead Comp., 1974, 1, 193-234.
6. Pike, R. M.; Sobinski, N.; McManus, P.J. Organopseudohalosilanes II. Azidosilanes. J. Organomet. Chem., 1983, 253, 183-216.
7. Pawlenko, S. Organo-Silicium Verbindungen, Houben-Weyl, Methoden der Organischen Chemie, Vol. XIII/5, Georg Thieme Verlag, Stuttgart-New York, 1980, pp. 123-132.
8. Sundermeyer, W. Silyltriazides. Angew. Chem., 1962, 74, 875.
9. Sundermeyer, W. Reactions in salt melts. IX. Preparation of silyl azides. Chem. Ber., 1963, 96, 1293-1297.
10. Sundermeyer, W. Dimethyldiazidosilane. Angew. Chem., 1962, 74, 717.
11. Washburne, S. S.; Peterson, W. R. Jr. Facile preparation of silyl azides with dipolar aprotic solvents. J. Organomet. Chem., 1971, 33, 153-156.
12. Birkofer, L.; Wegner, P. Trimethylsilyl azide. Org. Synth., 1970, 50, 107-108.
13. Ebsworth, E. A. V.; Mays, M. J. The preparation and properties of silyl azide. J. Chem. Soc., 1964, 3450-3454.
14. West, R.; Thayer, J. S. Organosilyl azides. J. Am. Chem. Soc., 1962, 84, 1763-1764.
15. Wiberg, N.; Neruda, B. Silylazides. V. Preparation, properties, and structure of some silyl azides. Chem. Ber., 1966, 99, 740-749.
16. Wiberg, N.; Raschig, F.; Sustmann, R. Preparation and properties of a triphenylsilyl azide. Angew. Chem., 1962, 74, 388-389.
17. Wiberg, N.; Raschig, F.; Sustmann, R. Silyl azides. II. Triphenylazidosilane and diphenyl-diazidosilane. Angew. Chem., 1962, 74, 716-717.
18. Connolly, J. W.; Urry, G. On the properties of trimethyl silyl azide. Inorg. Chem., 1962, 1, 718-719.
19. Thayer, J. S.; West, R. Trimethylazido compounds of group IVA elements. Inorg. Chem., 1964, 3, 889-893.
20. Sukata, K. Efficient synthesis of silyl azides using sodium azide impregnated on Amberlite XAD resin. J. Org. Chem., 1988, 53, 4867-4869.
21. Weidenbruch, M.; Pesel, H. Silicon compounds with strong intramolecular steric interactions, VII. Tri-tert-butylsilicon pseudohalides. Z. Naturfosch., 1978, 33B, 1465-1467.
22. Birkofer, L.; Ritter, A.; Richter, P. Preparation of trimethylsilyl azide. Angew. Chem. Int. Ed. Engl., 1962, 1, 267.
23. Rühlmann, K.; Reiche, A.; Becker, M. The silicon-nitrogen bond. XVI. Preparation of silylazides. Chem. Ber., 1965, 98, 1814-1818.
24. Ettenhuber, E.; Rühlmann, K. Silicon-nitrogen bonding. XXVIII. Reactions with azidosilanes. Chem. Ber., 1968, 101, 743-750.
25. Müller, H.; van Wazer, J. R. Redistribution equilibria involving fluoro and azido groups on the dimethylsilicon moiety. J. Organomet. Chem., 1970, 23, 395-402.
26. Moedritzer, K.; van Wazer, J. R. Silicon compounds. U. S. Pat., 1969, 3,466,314.
27. Birkofer, L.; Ritter, A.; Richter, P. Siliconorganic compounds. XIX. Thermolysis of silylated tetrazoles. Chem. Ber., 1963, 96, 2750-2757.
28. Wiberg, N.; Uhlenbrock, W. Diimide derivatives. 11. Silicon compounds. 19. Preparation and thermolysis of 1,1,4-tris(trimethylsilyl)-2-tetrazene. Chem. Ber., 1972, 105, 63-66.
29. Wiberg, N.; Bayer, H.; Ziegleder, G. Silicon compounds and their group homologs. Part 48. Preparation and some properties of silyl derivatives of hyponitrous acid and its amides. Z. Anorg. Allg. Chem., 1979, 459, 201-207.
30. Wiberg, N.; Bayer, H.; Vasisht, S. K. Tetrazene and its derivatives. Part 10. Preparation of silylated lithium tetrazenides. Chem. Ber., 1981, 114, 2658-2660.
31. 2 (E = silicon, germanium, or tin): preparation, characterization, and decomposition. Chem. Ber., 1979, 112, 2718-2729.
32. Seyferth, D.; Haas, C. K.; Lambert, R. L. Jr.; Annarelli, D.C. The extraordinary reactivity of the ring Si---C bonds in 1,1-dimethyl-trans-2,3-bis(2',2'-dimethylcyclopropylidene)-1-silacyclopr opane. J. Organomet. Chem., 1978, 152, 131-154.
33. Birkofer, L.; Ritter, A.; Uhlenbrauck, H. Siliconorganic compounds. XXI. Substitution and addition reactions with silylated acetylenes. Chem. Ber., 1963, 96, 3280-3288.
34. Birkofer, L.; Wegner, P. 1,3-Cycloadditions with trimethylsilyl azide. Isomeric N-acetyl-1,2,3-triazoles. Chem. Ber., 1966, 99, 2512-2517.
35. Tanaka, Y.; Velen, S. R.; Miller, S. I. Syntheses and properties of H-1,2,3-triazoles. Tetrahedron, 1973, 29, 3271-3283.
36. Bottaro, J. C.; Schmitt, R. J.; Bedford, C. D.; Gilardi, R.; George, C. Reactions of 1-nitro-2-(trialkylsilyl)acetylenes. J. Org. Chem., 1990, 55, 1916-1919.
37. Jenkins, S. M.; Wadsworth, H. J.; Bromidge, S.; Orlek, B. S.; Wyman, P. A.; Riley, G.J.; Hawkins, J. Substituent variation in azabicyclic triazole-and tetrazole-based muscarinic receptor ligands. J. Med. Chem., 1992, 35, 2392-2406.
38. Jin, T.; Kamijo, S.; Yamamoto, Y. Copper-catalysed synthesis of Nunsubstituted 1,2,3-triazoles from nonactivated terminal alkynes. Eur. J. Org. Chem., 2004, 3789-3791.
39. Scheiner, P. Triazoline photodecomposition. The preparation of aziridines. Tetrahedron, 1968, 24, 2757-2765.
40. Stout, D. M.; Takaya, T.; Meyers, A. I. An unequivocal synthesis of Nsubstituted 1,4-dihydropyridines. J. Org. Chem., 1975, 40, 563-569.
41. Washburne, S. S.; Peterson, W. R. Jr.; Berman, D. A. Reaction of trimethylsilyl azide with anhydrides and imides. A new uracil synthesis via nitrogen insertion. J. Org. Chem., 1972, 37, 1738-1742.
42. Bassindale, A. R.; Brook, A. G.; Jones, P. F.; Stewart, J. A. G. Bis(silyl)enamines or silylaziridines from the thermal reactions of azides with alkenylsilanes. J. Organomet. Chem., 1978, 152, C25-C28.
43. Washburne, S. S.; Peterson, W. R. Jr. Cycloaddition reactions of metal azides. Ferrocenyl-tetrazole via a silyl azide. J. Organomet. Chem., 1970, 21, 427-430.
44. Kikelj, D.; Neidlein, R. A convenient synthesis of 2-(1H-tetrazol-5-yl)-2-cyanoacetate betaines. Synthesis, 1993, 873-875.
45. Wittenberger, S. J.; Donner, B. G. Dialkyltin oxide mediated addition of trimethylallyl azide to nitriles. A novel preparation of 5-substituted tetrazoles. J. Org. Chem., 1993, 58, 4139-4141.
46. Jin, T.; Kitahara, F.; Kamijo, S.; Yamamoto, Y. Copper-catalyzed synthesis of 5-substituted 1H-tetrazoles via the [3+2] cycloaddition of nitriles and trimethylsilyl azide. Tetrahedron Lett., 2008, 49, 2824-2827.
47. Jin, T.; Kitahara, F.; Kamijo, S.; Yamamoto, Y. Synthesis of 5-substituted 1H-tetrazoles by the copper-catalyzed [3+2] cycloaddition of nitriles and trimethylsilyl azide. Chem. Asian J., 2008, 3, 1575-1580.
48. Bonnamour, J.; Bolm, C. Iron salts in the catalyzed synthesis of 5-substituted 1H-tetrazoles. Chem. Eur. J., 2009, 15, 4543-4545.
49. Sinitsa, A. D.; Parkhomenko, N. A.; Markovskii, L. N. Addition of trimethylsilyl azide to phenyl isocyanate and benzonitrile. Zh. Obshch. Khim., 1977, 47, 232.
50. Tsuge, O.; Urano, S.; Oe, K. Reactions of trimethylsilyl azide with heterocumulenes. J. Org. Chem., 1980, 45, 5130-5136.
51. Toselli, M.; Zanirato, P. Preparation and [2+3] cycloaddition of thienyl isocyanates with trimethylsilyl azide: one-pot synthesis of thienyltetrazolin-5-ones. J. Chem. Soc., Perkin Trans I, 1992, 1101-1104.
52. Floch, L.; Martvoň, A.; Uher, M.; Leško, J.; Weis, W. Reaction of isothiocyanates with azoimide and trimethylsilyl azide. Collect. Czech. Chem. Commun., 1977, 42, 2945-2952.
53. Tamura, Y.; Tsugoshi, T.; Mohri, S.-I.; Nakajima, Y.; Kita, Y. Cycloaddition to 1,3-dialkoxycarbonylallenes: one-step synthesis of heterocyclic compounds containing a dialkyl glutaconate structure. Chem. Pharm. Bull., 1985, 33, 3257-3262.
54. 2) in the presence of silaethene trapping reagents. Chem. Ber., 1981, 114, 3518-3532.
55. 2E=NR (E= Si, Ge) from sila-and germadihydrotriazoles. Chem. Ber., 1987, 120, 1203-1212.
56. 2E=NR (E= Si, Ge) by way of sila-or germadihydrotetrazoles. Chem. Ber., 1987, 120, 1213-1221.
57. 2. Chem. Ber., 1995, 128, 1231-1240.
58. 3: preparation, stability and reactivity. J. Organomet. Chem., 1988, 341, 145-163.
59. 3. Z. Naturforsch. B, 1987, 42, 1055-1061.
60. Rösch, W.; Facklam, T.; Regitz, M. Phosphorus compounds with unusual coordination-20. 1,2,3,4-triazaphospholes by [3+2]-cycloaddition of azides to a stable phosphaalkyne. Tetrahedron, 1987, 43, 3247-3256.
61. Birkofer, L.; Kaiser, W. Addition of trimethylsilyl azide to aldehydes and epoxides. Liebigs Ann. Chem., 1975, 266-274.
62. Birkofer, L.; Müller, F.; Kaiser, W. Silicon-organic compounds. XXXIII. Reaction of aldehydes with trimethylsilyl azide. Tetrahedron Lett., 1967, 8, 2781-2783.
63. Evans, D. A.; Truesdale, L. K. Carbonyl insertion reactions of silicon pseudohalides: catalysis. Tetrahedron Lett., 1973, 14, 4929-4932.
64. Kyba, E. P.; John, A. M. Primary alkyl amines. Generation by reduction of α-alkoxyazides. Tetrahedron Lett., 1977, 18, 2737-2740.
65. Nishiyama, K.; Watanabe, A. A novel synthesis of aromatic nitrile by the reaction of aromatic aldehyde with trimethylsilyl azide. Chem. Lett., 1984, 773-774.
66. Nishiyama, K.; Watanabe, A. Addition reaction of trimethylsilyl azide towards ketones and facile formation of tetrazole derivatives. Chem. Lett., 1984, 455-458.
67. Nishiyama, K.; Yamaguchi, T. Selective formation of alkyl azides using trimethylsilyl azide and carbonyl compounds. Synthesis, 1988, 106-108.
68. Blandy, C.; Choukroun, R.; Gervais, D. Synthesis of O-protected azidohydrins catalyzed by titanium and vanadium complexes. Tetrahedron Lett., 1983, 24, 4189-4192.
69. Meguro, M.; Asao, N.; Yamamoto, Y. Ytterbium triisopropoxide catalysed ring opening of epoxides with trimethylsilyl azide. J. Chem. Soc., Chem. Comm., 1995, 1021-1022.
70. Sutowardoyo, K. I.; Emziane, M.; Lhoste, P.; Sinou, D. Highly regio and chemoselective ring opening of epoxides with trimethylsilyl azide in the presence of aluminium isopropoxide and titanium isopropoxide. Tetrahedron, 1991, 47, 1435-1446.
71. Van de Veghe, P.; Collin, J. Ring opening reactions of epoxides catalyzed by samarium iodides. Tetrahedron Lett., 1995, 36, 1649-1652.
72. Fujiwara, M.; Tanaka, M.; Baba, A.; Ando, H.; Souma, Y. Tetraphenylstibonium hydroxide-catalyzed reaction of trimethylsilyl azide with oxiranes. Tetrahedron Lett., 1995, 36, 4849-4852.
73. 3. An efficient, catalytic route to 1,2-amino alcohols. J. Am. Chem. Soc., 1996, 118, 7420-7421.
74. Kantam, M. L.; Santhi, P. L.; Prasad, K. V. R.; Figueras, F. Iron pillared clay-an efficient catalyst for ring opening of oxiranes. J. Mol. Catal. A: Chemical, 2000, 156, 289-292.
75. Kantam, M. L.; Choudary, B. M.; Bharathi, B. Ring opening of oxiranes catalyzed by Mn-salen immobilized mesoporous materials. Synth. Comm., 1999, 29, 1121-1128.
76. 5-dioxaphospholane methodology. J. Org. Chem., 1992, 57, 3409-3413.
77. Leung, W.-H.; Yu, M.-T.; Wu, M.-C.; Yeung, L.-L. Molecular sieves promoted regioselective ring opening of N-tosylaziridines catalyzed by imidochromium complexes. Tetrahedron Lett., 1996, 37, 891-892.
78. Li, Z.; Fernandez, M.; Jacobsen, E.N. Enantioselective ring opening of meso aziridines catalyzed by tridentate Schiff base chromium(III) complexes. Org. Lett., 1999, 1, 1611-1613.
79. Ferraris, D., Drury III, W. J.; Cox, C.; Lectka, T. "Orthogonal" Lewis acids: catalyzed ring opening and rearrangement of acylaziridines. J. Org. Chem., 1998, 63, 4568-4569.
80. 3 or TMSCN catalyzed by discrete yttrium complexes. Angew. Chem. Int. Ed., 2009, 48, 1126-1129.
81. Wu, J.; Hou, X.-L.; Dai, L.-X. Effective ring-opening reaction of aziridines with trimethylsilyl compounds: a facile access to β-amino acids and 1,2-diamine derivatives. J. Org. Chem., 2000, 65, 1344-1348.
82. Chandrasekhar, M.; Sekar, G.; Singh, V.K. An efficient method for opening nonactivated aziridines with TMS azide: application in the synthesis of chiral 1,2-diaminocyclohexane. Tetrahedron Lett., 2000, 41, 10079-10083.
83. Wu, B.; Parquette, J. R.; RajanBabu, T. V. Regiodivergent ring opening of chiral aziridines. Science, 2009, 326, 1662.
84. Kricheldorf, H.R. Reactions with silyl azides, 5. Acylation and alkylation of trimethylsilyl azide. Chem. Ber., 1973, 106, 3765-3768.
85. Praly, J.-P.; Kharaff, Z.E.; Descotes, G. Syntheses of anomeric glucopyranosylidene diazides. J. Chem. Soc., Chem. Comm., 1990, 431-432.
86. Yin, J.; Linker, T. Convenient synthesis of bicyclic carbohydrate 1,2-lactones and their stereoselective opening to 1-functionalized glucose derivatives. Chem. Eur. J., 2009, 15, 49-52.
87. Kirchmeyer, S.; Mertens, A.; Olah, G.A. Synthetic methods and reactions; 115. Conversion of acetals and ketone acetals into azido compounds using trimethylsilyl azide. Synthesis, 1983, 500-502.
88. Nishiyama, K.; Karigomi, H. Reaction of trimethylsilyl azide with organic halides. Chem. Lett., 1982, 1477-1478.
89. Ito, M.; Koyakumaru, K.; Ohta, T.; Takaya, H. A simple and convenient synthesis of alkyl azides under mild conditions. Synthesis, 1995, 376-378.
90. Soli, E.D.; Manoso, A.S.; Patterson, M.C.; DeShong, P.; Favor, D.A.; Hirschmann, R.; Smith, A.B. III Azide and cyanide displacements via hypervalent silicate intermediates. J. Org. Chem., 1999, 64, 3171-3177.
91. Prakash, G.K.S.; Stephenson, M.A.; Shih, J.G.; Olah, G.A. Preparation of secondary and tertiary cyclic and polycyclic hydrocarbon azides. J. Org. Chem., 1986, 51, 3215-3217.
92. Sasaki, T.; Nakanishi, A.; Ohno, M. Synthesis of adamantane derivatives. 56. Reaction of 1-adamantyl chloride with trimethylsilyl pseudohalide. J. Org. Chem., 1981, 46, 5445-5447.
93. Aoyama, M.; Hara, S. Synthesis of functionalized adamantanes from fluoroadamantanes. Tetrahedron, 2009, 65, 3682-3687.
94. Pearson, W. H.; Schkeryantz, J. M. Lithium perchlorate-assisted substitution reactions of allylic acetates and allylic alcohols. J. Org. Chem., 1992, 57, 2986-2987.
95. Grieco, P. A.; Handy, S. T. Magnesium trifluoromethanesulfonimide(triflimide) promoted substitution reactions of allylic and benzylic acetates. Magnesium triflimide as a substitute for magnesium perchlorate. Tetrahedron Lett., 1997, 38, 2645-2648.
96. Safi, M.; Fahrang, R.; Sinou, D. Palladium(0)-catalyzed azidation of allyl esters with trimethylsilyl azide. Tetrahedron Lett., 1990, 31, 527-530.
97. Koziara, A.; Zwierzak, A. Iminophosphorane-mediated transformation of tertiary alcohols into t-alkylamines and their N-phosphorylated derivatives. Tetrahedron Lett., 1987, 28, 6513-6516.
98. He, L.; Wanunu, M.; Byun, H.-S., Bittman, R. Regioselective and stereospecific azidation of 1,2-and 1,3-diols by azidotrimethylsilane via a Mitsunobu reaction. J. Org. Chem., 1999, 64, 6049-6055.
99. 3 and alkynes. Tetrahedron Lett., 2007, 48, 5831-5834.
100. Kricheldorf, H. R. Reactions with silylazides. 1. Synthesis of isocyanates from carboxylic acid chlorides and trimethylsilylazide. Synthesis, 1972, 551-553.
101. Khoukhi, M.; Vaultier, M.; Benalil, A.; Carboni, B. Curtius rearrangement of ω-azido acid chlorides: access to the corresponding ω-azido substituted amines and carbamates, useful building blocks for polyamine syntheses. Synthesis, 1996, 483-487.
102. MacMillan, J. H.; Washburne, S. S. Interaction of carbonyl compounds with organometallic azides. V. Sorboyl chloride and its conversion to an α-pyridone. J. Org. Chem., 1973, 38, 2982-2984.
103. Peterson, W. R. Jr.; Radell, J.; Washburne, S. S. Interaction of carbonyl compounds with organometallic azides IV. Perfluoroalkyl isocyanates. J. Fluorine Chem., 1973, 2, 437-441.
104. Washburne, S.S.; Peterson, W.R. Jr. Curtius degradation utilizing trimethylsilyl azide. Facile isocyanate synthesis. Synth. Comm., 1972, 2, 227-230.
105. Prakash, G.K.S.; Iyer, P.S.; Arvanaghi, M.; Olah, G.A. Zinc iodide catalyzed preparation of aroyl azides from aroyl chlorides and trimethylsilyl azide. J. Org. Chem., 1983, 48, 3358-3359.
106. Farooq, O.; Wang, Q.; Wu, A.; Olah, G. A. Preparation of tertiary alkyl isocyanates by the zinc iodide catalyzed reaction of tertiary alkanoyl chlorides with trimethylsilyl azide. J. Org. Chem., 1990, 55, 4282-4283.
107. Kricheldorf, H. R. Reactions with silylazides. 3. Azidoformic acid esters and N-acylphosphinimines. Synthesis, 1972, 695-697.
108. Lee, J.G.; Kwak, K.H. Oxidation of aldehydes to acyl azides by chromic anhydride-azidotrimethylsilane. Tetrahedron Lett., 1992, 33, 3165-3166.
109. Kricheldorf, H. R. Reactions with silyl azides, 2. Azidolysis of anhydrides. Chem. Ber., 1972, 105, 3958-3965.
110. Washburne, S. S.; Peterson, W. R. Jr.; Berman, D. A. Reaction of trimethylsilyl azide with anhydrides and imides. A new uracil synthesis via nitrogen insertion. J. Org. Chem., 1972, 37, 1738-1742.
111. Kricheldorf, H. R. Synthesis and polymerization of β-amino acid Ncarboxyanhydrides. Makromol. Chem., 1973, 173, 13-41.
112. Kricheldorf, H. R.; Regel, W. Reactions with silyl azides. 4. Cyclopropyl isocyanates. Chem. Ber., 1973, 106, 3753-3764.
113. Kricheldorf, H.R. Polyaddition and cyclization of 5-isocyanatocarboxylic acids. Makromol. Chem., 1975, 176, 2755-2759.
114. Kricheldorf, H.R. Reactions with silylazides. 7. Trimethylsilyl 4-isocyanatocarboxylates and 4-aminocarboxylic acid N-carboxylic acid anhydrides. Makromol. Chem., 1975, 176, 57-79.
115. Warren, J.D.; MacMillan, J.H.; Washburne, S.S. Synthesis of substituted 2H-1,3-oxazine-2,6-diones by reaction of trimethylsilyl azide with maleic anhydrides. J. Org. Chem., 1975, 40, 743-746.
116. Moriarty, R.M.; Hou, K.-C.; Miller, R.S. Conversion of dimethyl acetals of α-hydroxy-acetophenones and α-hydroxypropiophenone to monoazides and tetrazoles using trimethylsilyl azide. Synthesis, 1984, 683-685.
117. Sandberg, M.; Sydnes, L.K. The chemistry of acetals. Part II. Formation of nitriles by treatment of acylals with trimethylsilyl azide in the presence of a Lewis acid. Tetrahedron Lett., 1998, 39, 6361-6364.
118. Fraenk, W.; Habereder, T.; Hammerl, A.; Klapötke, T.M.; Krumm, B.; Mayer, P.; Nöth, H.; Warchhold, M. Highly energetic tetraazidoborate anion and boron triazide adducts. Inorg. Chem., 2001, 40, 1334-1340.
119. Wiberg, N.; Joo, W.C.; Schmid, K.H. On some azides of beryllium, magnesium, boron, and aluminium (on the reaction of silylazides with element halides). Z. Anorg. Allg. Chem., 1972, 394, 197-208.
120. Wiberg, N.; Schmid, K.H. Inorganic azides. VII. Preparation and properties of dichloro tin diazide. Chem. Ber., 1967, 100, 748-754.
121. Schulz, A.; Villinger, A. Staudiger reaction as a way out to avoid cyclization in the reaction of silylated dichloro(hydrazino)phosphane with trimethylsilyl azide. Eur. J. Inorg. Chem., 2008, 4199-4203.
122. Michalik, D.; Schulz, A., Villinger, A.; Weding, N. A cationic cyclic phosphorus(III) azide. Angew. Chem. Int. Ed. Engl., 2008, 47, 6465-6468.
123. Skowronska, A.; Pakulski, M.; Michalski, J. Reaction between chlorophosphoranes and benzyltri-n-butylammonium or trimethylsilyl azides. Direct observation of hexacoordinate intermediates in displacement reactions at pentacoordinate phosphorus. J. Am. Chem. Soc., 1979, 101, 7412-7413.
124. Scherer, O.J.; Kuhn, N. Organoelement amine-imine compounds. XIII. Bis[(trimethylsilyl)amino][(trimethylsilyl)imino]phosphine and bis[(trimethylsilyl)amino]bis[(trimethylsilyl)imino]phosphorane. Chem. Ber., 1974, 107, 2123-2125.
125. Kratzer, R.H.; Paciorek, K.L. Reactions of chlorophosphines with silyl azides. Inorg. Chem., 1965, 4, 1767-1771.
126. 6]. Angew. Chem. Int. Ed. Engl., 2004, 43, 6676-6680.
127. 5 species (M = As, Sb). J. Fluorine Chem., 2001, 109, 151-162.
128. Wiberg, N.; Schmid, K.H. Inorganic azides. VI. Tetrachloro antimony azide. Chem. Ber., 1967, 100, 741-747.
129. Wiberg, N.; Schmid, K.H. Silyl azides. IV. The reaction of silyl azides with antimony pentachloride. Angew. Chem., 1964, 76, 380-381.
130. 3. J. Am. Chem. Soc., 2004, 126, 710-711.
131. Klapötke, T.M.; Krumm, B.; Scherr, M. Studies on the properties of organoselenium(IV) fluorides and azides. Inorg. Chem., 2008, 47, 4712-4722.
132. 2-. Angew. Chem. Int. Ed. Engl., 2007, 46, 8686-8690.
133. 3 and of an unusual tellurium(VI) fluoride salt. Z. Anorg. Allg. Chem., 2007, 633, 1618-1626.
134. Klapötke, T.M.; Krumm, B.; Mayer, P.; Scherr, M. Synthesis and structures of cycloalkanetellurium(IV) fluorides and azides. Z. Naturforsch. B: Chem. Sci., 2006, 61, 528-534.
135. Wiberg, N.; Schwenk, G.; Schmid, K.H. Tellurium trichloride azide and tellurium dichloride diazide (reaction of trimethylsilyl azide with chalkogen halides). Chem. Ber., 1972, 105, 1209-1215.
136. -. Angew. Chem. Int. Ed. Engl., 2003, 42, 5843-5846.
137. 5]. Angew. Chem. Int. Ed. Engl., 2003, 42, 5847-5851.
138. Schmidbaur, H.; Wolfsberger, W. Isosteric organometallic compounds. IV. Metal alkyl complexes of N-silylphosphineimides. Chem. Ber., 1967, 100, 1000-1015.
139. Birkofer, L.; Kim, S.M. Preparation of trialkylphosphinimines. Chem. Ber., 1964, 97, 2100-2101.
140. Itoh, K.; Okamura, M.; Ishii, Y. Reactions of group IV organometallic compounds. XXVII. Some reactions of [(trimethylsilyl)imino]phosphorane. J. Organomet. Chem., 1974, 65, 327-334.
141. 3. J. Organomet. Chem., 1974, 71, 159-164.
142. Appel, R.; Milker, R. Nonmetallic imine compounds. 54. Synthesis and reactions of silylated iminodiphosphanes. Chem. Ber., 1974, 107, 2658-2670.
143. Paciorek, K.L.; Kratzer, R.H. Reactions of triphenylsilyl azide with tetraphenyldiphosphine and diphenylphosphine. J. Org. Chem., 1966, 31, 2426-2427.
144. Schlak, O.; Stadelmann, W.; Stelzer, O.; Schmutzler, R. Side reactions in the interaction of trimethylsilyl azide with trimethylphosphite and tris(dimethylamino)phosphine. Z. Anorg. Allg. Chem., 1976, 419, 275-282.
145. Flindt, E.-P.; Rose, H.; Marsmann, H.C. Trivalent-pentavalent phosphorus compounds/phosphazenes. II. Synthesis of N-silylated phosphinimines. Z. Anorg. Allg. Chem., 1977, 430, 155-160.
146. Flindt, E.-P.; Rose, H. Trivalent-pentavalent phosphorus compounds/ phosphazenes. I. A new method for preparation of poly[bis(trifluorethoxy)phosphazenes]. Z. Anorg. Allg. Chem., 1977, 428, 204-208.
147. 2Si=NR]. J. Organomet. Chem., 1976, 110, C1-C4.
148. Patil, K.C.; Rao, C.N.R. Thermal decomposition of phenylazido compounds of group IVA elements. Indian J. Chem., 1968, 6, 220-222.
149. Gaidis, J.M.; West, R. Synthesis of a silazarophenanthrene. J. Am. Chem. Soc., 1964, 86, 5699-5700.
150. Klein, D.W.; Connolly, J.W. Photolysis of silyl azides. J. Organomet. Chem., 1971, 33, 311-319.
151. 2Si=NR]. J. Am. Chem. Soc., 1976, 98, 618-620.
152. Zigler, S.S.; Johnson, L.M.; West, R. Generation of silanimines by photolysis of hindered azidosilanes. J. Organomet. Chem., 1988, 341, 187-198.
153. Radziszewski, J.G.; Kaszynski, P.; Littmann, D.; Balaji, V. Hess, B.A. Jr.; Michl, J. Twisted Si=N bonds: matrix isolation of bridgehead silanimines. J. Am. Chem. Soc., 1993, 115, 8401-8408.
154. Sekiguchi, A.; Ando, W.; Honda, K. Matrix isolation of a silicon-nitrogen double bonded silaimine. Chem. Lett., 1986, 1029-1032.
155. Zigler, S.S.; West, R.; Michl, J. Observation of a silanimine in an inert matrix and in solution at low temperature. Chem. Lett., 1986, 1025-1028.
156. Maier, G.; Glatthaar, J. Silane nitrile: matrix isolation, adduct with hydrogen. Angew. Chem. Int. Ed. Engl., 1994, 33, 473-475.
157. Kuhn, A.; Sander, W. Photochemistry of dimethylsilyl azide: formation and reactivity of 1,1-dimethylsilanimine. Organometallics, 1998, 17, 248-254.
158. Kuhn, A.; Sander, W. Photochemistry of matrix-isolated phenylsilyl azides. Organometallics, 1998, 17, 4776-4783.
159. Perutz, R.N. Matrix photolysis of trimethylazidosilane: silicon-hydrogen bond formation. J. Chem. Soc., Chem. Comm., 1978, 762-763.
160. Ogilvie, J.F. Photodecomposition of trimethylsilyl azide in solid argon. Nature, 1968, 218, 1248-1249.
161. Maier, G.; Glatthaar, J.; Reisenauer, H.P. Hetero π-systems. 17. Aminosilylene (aminosilanediyl). Chem. Ber., 1989, 122, 2403-2405.
162. Gillette, G.R.; West, R. Reactions of tetramesityldisilene with azides: synthesis of disilaaziridines. J. Organomet. Chem., 1990, 394, 45-55.
163. 3. Tetrahedron Lett., 2008, 49, 4742-4745.
164. Sato, N.; Miwa, N.; Hirokawa, N. Studies on pyrazines. Part 27. A new deoxidative nucleophilic substitution of pyrazine N-oxides; synthesis of azidopyrazines with trimethylsilyl azide. J. Chem. Soc., Perkin Trans I, 1994, 885-888.
165. Nishiyama, K.; Miyata, I. Reaction of trimethylsilyl azide with C=N-O bond. Bull. Chem. Soc. Japan, 1985, 58, 2419-2420.
166. Jin, T.; Kamijo, S.; Yamamoto, Y. Synthesis of 1-substituted tetrazoles via the acid-catalyzed [3+2] cycloaddition between isocyanides and trimethylsilyl azide. Tetrahedron Lett., 2004, 45, 9435-9437.
167. Kamijo, S.; Jin, T.; Yamamoto, Y. Palladium-catalyzed selective synthesis of 2-allyltetrazoles. J. Org. Chem., 2002, 67, 7413-7417.
168. 3: synthesis of 1,5-disubstituted tetrazoles. J. Org. Chem., 2007, 72, 1852-1855.
169. Nayak, M.; Batra, S. Isonitriles from the Baylis-Hillman adducts of acrylates: viable precursor to tetrazolo-fused diazepinones via post-Ugi cyclization. Tetrahedron Lett., 2010, 51, 510-516.
170. 3SiNCS. Spectrochim. Acta, 1978, 34A, 719-730.
171. Durig, D.T.; Durig, M.S.; Durig, J.R. On the vibrational spectra and structural parameters of methyl, silyl, and germyl azide from theoretical predictions and experimental data. Spectrochim. Acta A, 2005, 61, 1287-1306.
172. Cradock, S.; Ebsworth, E.A.V.; Murdoch, J.D. Photoelectron spectra of some group 4 pseudohalides and related compounds. J. Chem. Soc., Faraday Trans 2, 1972, 68, 86-100.
173. Guimon, C.; Pfister-Guillouzo, G. Theoretical and experimental studies of the flash pyrolysis of trimethylsilyl azide and trimethylgermyl azide: generation and He I photoelectron spectra of iminosilylene and iminogermylene. Organometallics, 1987, 6, 1387-1392.
174. 14N-NMR spectra of some organometallic azides. J. Organomet. Chem., 1973, 51, 119-123.
175. Herges, R.; Starck, F. Synthesis and fragmentation of 2,2-diazido-1,3,2-dioxasila-5-cycloheptenes. J. Am. Chem. Soc., 1996, 118, 12752-12757.
176. 3. Asian Chem. Lett., 2003, 7, 69-72.
177. 2NCN. Chem. Phys. Lett., 1974, 28, 290-293.
178. Dakkouri, M.; Oberhammer, H. Determination of the molecular structure of trimethylazidosilane by gas electron diffraction. Z. Naturforsch. A, 1972, 27, 1331-1335.
179. Corey, E.R.; Cody, V.; Glick, M.D.; Radonovich, L.J. Azidotriphenylsilane: a group IVA-azide covalent bond. J. Inorg. Nucl. Chem., 1973, 35, 1714-1717.
180. Wharf, I.; Bélanger-Gariépy, F. Azidotriphenylsilane: a new determination. Acta Cryst. Sect. E, 2004, E60, o1643-o1645.
181. Zigler, S.S.; Haller, K.J.; West, R. Structures of two organosilyl azides. Organometallics, 1989, 8, 1656-1660.
182. Palmer, M.H.; Nelson, A.D. The structures of the azido-, isocyanato-and isothiocyanato-derivatives of methane and silane and their derivatives. A comparison of ab initio with experimental results. J. Mol. Struct., 2003, 660, 49-65;2004,689,161-173.
183. Maier, G.; Reisenauer, H.P.; Glatthaar, J. Reactions of silicon atoms with nitrogen: a combined matrix spectroscopic and density functional theory study. Organometallics, 2000, 19, 4775-4783.
184. Kricheldorf, H.R.; Leppert, E. Reaction with silylazides. 9. Trimethylsilyl azidosulfate and trimethylsilyl amidosulfate. Synthesis, 1975, 49-50.
185. Ando, W.; Tsumaki, H.; Ikeno, M. Photolysis of diazidosilanes. Generation and reactions of digonal silicon intermediates such as silacarbodi-imides. J. Chem. Soc., Chem. Comm., 1981, 597-598.
186. Ohtaki, T.; Kabe, Y.; Ando, W. Reactions of bis[bis(trimethylsilyl)methyl]germylene and the corresponding stannylene with diazidosilanes. Heteroatom Chem., 1994, 5, 313-320.
187. Ohtaki, T.; Ando, W. Formation of strained cyclic azapolysila compounds via N-(azidosilyl)germanimines and stannanimines. Chem. Lett., 1994, 1061-1064.
188. Elmorsy, S.S.; El-Ahl, A.-A.S.; Soliman, H.; Amer, F.A. Synthesis of triazidochlorosilane (TACS). A novel silicon mediated one pot conversion of aldehydes to nitriles. Tetrahedron Lett., 1995, 36, 2639-2640.
189. Elmorsy, S.S. Oxidation of aldehydes to acyl azides using triazidochlorosilane (TACS)-active manganese dioxide reagent. Tetrahedron Lett., 1995, 36, 1341-1342.
190. El-Ahl, A.-A.S.; Elmorsy, S.S.; Soliman, H.; Amer, F.A. A facile and convenient synthesis of substituted tetrazole derivatives from ketones or α, β-unsaturated ketones. Tetrahedron Lett., 1995, 36, 7337-7340.
191. Mphahlele, M. J. Reaction of ring and side chain substituted 3-phosphonomethylcyclohexenones with azidosilane reagents. Phosphorus, Sulfur, and Silicon, 1996, 118, 145-154.
192. El-Ahl, A.-A.S.; Elmorsy, S.S.; Elbeheery, A.H.; Amer, F.A. A novel approach for the synthesis of 5-substituted tetrazole derivatives from primary amides in mild one-step method. Tetrahedron Lett., 1997, 38, 1257-1260.
193. Bock, H.; Dammel, R. Phenyl silaisocyanide: the first organosilicon compound with a formal Si≡N triple bond. Angew. Chem. Int. Ed. Engl., 1985, 24, 111-112.
194. Radziszewski, J.G.; Littmann, D.; Balaji, V.; Fabry, L.; Gross, G.; Michl, J. Multiply bonded silicon: matrix isolation and chemical trapping of products of pyrolysis and photolysis of triazidophenylsilane. Organometallics, 1993, 12, 4816-4824.
195. Itagaki, Y.; Iseoka, T.; Iida, T.; Ohshita, J.; Shiotani, M.; Kunai, A. An ESR study on structures of a series of silylnitrenes. Chem. Phys. Lett., 2001, 348, 249-254.
196. n (n = 3,4). J. Phys. Chem. A, 2005, 109, 9089-9094.
197. Filippou, A.C.; Portius, P.; Schnakenburg, G. The hexaazidosilicate(IV) ion: synthesis, properties, and molecular structure. J. Am. Chem. Soc., 2002, 124, 12396-12397.
198. Ruidisch, I.; Schmidt, M. Methylgermanylazide. J. Organomet. Chem., 1964, 1, 493-494.
199. Cradock, S.; Ebsworth, E.A.V. Germyl chemistry. II. Exchange reactions of silyl and germyl halides. J. Chem. Soc. A, 1967, 1226-1229.
200. Cradock, S.; Ebsworth, E.A.V. Studies in germyl chemistry. Part IV. Germyl azide. J. Chem. Soc. A, 1968, 1420-1426.
201. Drake, J.E.; Hemmings, R.T. Preparation and characterization of pseudohalogeno(methyl)germanes and related compounds. Can. J. Chem., 1973, 51, 302-311.
202. Barker, G.K.; Drake, J.E.; Hemmings, R.T. Characterization of monohalogen and monopseudohalogen derivatives of dimethylgermane. Can. J. Chem., 1974, 52, 2622-2633.
203. Zhou, Q.; Weber, W.P. Exchange reactions between trimethylsilyl azide and hexamethyldigermoxane. J. Organomet. Chem., 1988, 342, 291-294.
204. 2, the first structural example of a phosphoranimine phosphine complex. Inorg. Chem., 1990, 29, 808-814.
205. 3: spectroscopic characterization and density functional computations. Inorg. Chem., 1996, 35, 4995-4998.
206. Schmidbaur, H.; Wolfsberger, W. Reaction of methylstannyl and methylgermanyl azides with phosphines. Chem. Ber., 1968, 101, 1664-1669.
207. Wolfsberger, W. N-Trimethylgermyl triorganophosphine imines. Z. Naturforsch., 1977, 32b, 152-156.
208. Tsai, T.-T.; Lehn, W.L.; Marshall, C.J. Jr. Reactions of triphenylsilicon,-germanium and-tin azides with their corresponding hydrides. J. Organomet. Chem., 1970, 22, 387-393.
209. Baceiredo, A.; Bertrand, G.; Mazerolles, P. Photolytic rearrangement of germanium azides. Evidence for transient germa-imines. Tetrahedron Lett., 1981, 22, 2553-2556.
210. Veith, M.; Werle, E.; Huch, V. Reaction of a cyclic bis(amino)germylene with germaniumazides: trapping-reactions of unstable germa-imines. Z. Anorg. Allg. Chem., 1993, 619, 641-651.
211. Raj, P.; Ranjan, A.; Singhai, K. Cycloaddition reactions of unsaturated substrates with a germanium nitrogen bond. Synth. React. Inorg. Metal-Org. Chem., 1984, 14, 477-484.
212. Sullivan, J.F.; Durig, J.R. Structural determinations and normal coordinate analysis of some germanium pseudohalogens. J. Mol. Struct., 1980, 60, 37-42.
213. 3. J. Mol. Struct., 1981, 72, 41-55.
214. Durig, J.R.; Sullivan, J.F.; Li, Y.S.; Mohamad, A.B. The microwave spectra and structure of germylazide and germylisocyanate. J. Mol. Struct., 1982, 79, 235-238.
215. Groner, P.; Attia, G.M.; Mohamad, A.B.; Sullivan, J.F.; Li, Y.S.; Durig, J.R. Microwave spectrum, dipole moment, barrier to internal rotation, and molecular structure of germylazide. J. Chem. Phys., 1989, 91, 1434-1439.
216. Murdoch, J.D.; Rankin, D.W.H. Gas phase structures of three germyl pseudohalides. J. Chem. Soc., Chem. Comm., 1972, 748-750.
217. Palmer, M.H. The structures of the azido-, isocyanato-and isothiocyanatoderivatives of germane, stannane and plumbane and their trimethyl derivatives: a comparison of ab initio results with experiment, and with the methane and silane analogs. J. Mol. Struct., 2004, 692, 43-56.
218. Thayer, J.S.; Strommen, D.P. Some infrared studies of organometallic pseudohalogens. J. Organomet. Chem. 1966, 5, 383-387.
219. 3GeNCS. J. Raman Spectrosc. 1981, 11, 459-468.
220. Preston, P.N.; Sutcliffe, L.H.; Taylor, B. NMR investigation of tetraphenyl-, vinyltriphenyl-, azidotriphenyl-, and dihalodiphenyl-derivatives of fourth main group elements. Spectrochim. Acta, 1972, 28A, 197-210.
221. Drake, J.E.; Riddle, C.; Coatsworth, L. An ESCA investigation of some halogeno(methyl)-silane and-germane series. Can. J. Chem., 1975, 53, 3602-3612.
222. Cavell, R.G.; Katti, K.V. New inorganic and organometallic heterocyclic compounds derived from novel heterodifunctional phosphorus-nitrogen ligands. Phosphorus, Sulfur, Silica, 1989, 41, 43-50.
223. Veith, M.; Werle, E. Cyclic diazastannylenes. XXXII. On the synthesis and reactivity of difunctional cyclosilagermadiazanes-formation of digermanes. Z. Anorg. Allg. Chem., 1992, 609, 19-28.
224. Barrau, J.; Bean, D.L.; Welsh, K.M.; West, R.; Michl, J. Photochemistry of a matrix-isolated geminal diazide. Dimethylgermylene. Organometallics, 1989, 8, 2606-2608.
225. Miller, F.A. Molecules we have recently met. Appl. Spectr., 1975, 29, 461-469.
226. Jensen, J.O. Vibrational frequencies and structural determination of tetraazidogermane. Spectrochim. Acta Part A, 2003, 59, 2805-2814.
227. Koroteev, P.S.; Egorov, M.P.; Nefedov, O.M.; Alexandrov, G.G.; Nefedov, S.E.; Eremenko, I.L. Synthesis and structure of bis(acetylacetonato)germanium(IV) diazide. Russ. Chem. Bull., 2000, 49, 1800-1801.
228. 2(TMEDA)]. New J. Chem., 2002, 26, 803-805.
229. Filippou, A.C.; Portius, P.; Neumann, D.U.; Wehrstedt, K.-D. The hexaazidogermanate(IV) ion: synthesis, structures, and reactions. Angew. Chem. Int. Ed. Engl., 2000, 39, 4333-4336.
230. 3: a convenient route to six-co-ordinate triazidogermanium(IV) compounds. J. Chem. Soc., Dalton Trans., 2000, 1759-1768.
231. 3 [Tp'= hydrotris(3,5-dimethylpyrazol-1-yl)borato]. Chem. Commun., 1998, 2327-2328.
232. 3 featuring heterobicyclic 10-π-electron ring systems. Inorg. Chem., 2000, 39, 4147-4151.
233. 2CH). Inorg. Chem., 2001, 40, 1000-1005.
234. Schmidt, H.; Keitemeyer, S.; Neumann, B.; Stammler, H.-G.; Schoeller, W.W.; Jutzi, P. Germylenes and germyl cations with the 2,4-di-tert-butyl-6-(N, N-dimethylaminomethyl)phenyl ligand. Organometallics. 1998, 17, 2149-2151.
235. 14 = Ge, Sn): synthesis and structure. J. Organomet. Chem., 2005, 690, 1056-1062.
236. Herr, R.J. 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods. Bioorg. and Medicinal Chem., 2002, 10, 3379-3393.
237. Mita, T.; Fukuda, N.; Roca, F.X.; Kanai, M.; Shibasaki, M. Second generation catalytic asymmetric synthesis of Tamiflu: allylic substitution route. Org. Lett., 2007, 9, 259-262.
238. 3. J. Am. Chem. Soc., 2006, 128, 6312-6313.