12
1 Nitrile Imines and Their Properties
65. Castan F, Baceiredo A, Bigg D, Bertrand G (1991) Synthesis and reactivity of stable silylsubstituted nitrilimines. J Org Chem 56:1801–1807
66. Bertrand G, Wentrup C (1994) Nitrile imines: from matrix characterization to stable
compounds. Angew Chemie Int Ed English 33:527–545
67. Leue C, Reau R, Neumann B, Stammler H-G, Jutzi P, Bertrand G (1994) Preparation of monoand bis(germyl) nitrilimines from germylenes and stannyl diazo derivatives. Organometallics
13:436–438
68. Sicard G, Baceiredo A, Bertrand G (1988) Synthesis and reactivity of a stable nitrile imine. J
Am Chem Soc 110:2663–2664
69. Müller E, Disselhoff H (1933) Über die Einwirkung von natrium auf aliphatische
diazoverbindungen. Naturwissenschaften 21:661
70. Müller E, Disselhoff H (1934) Studies on diazomethanes I. Justus Liebig’s Ann der Chemie
512:250–263
71. Müller E, Kreutzmann W (1934) Studies on diazomethanes II. Justus Liebig’s Ann der Chemie
512:264–275
72. Müller E, Ludsteck D (1954) Studies on diazomethanes III: preparation of isodiazomethane
and its rearrangement to diazomethane. Chem Ber 87:1887–1895
73. Müller E, Ludsteck D (1955) Studies on diazomethanes V: reactive behavior of
diazomethyllithium. Chem Ber 88:921–933
74. Müller E, Rundel W (1957) Studeis on diazomethanes IX. Another recent synthesis of
diazomethane and isodiazomethane. Chem Ber 90:2673–2678
75. Müller E, Kästner P, Rundel W (1965) Studies on diazomethanes XXII: The structure of
isodiazomethane. Chem Ber 98:711–714
76. Müller E, Kästner P, Beutler R, Rundel W, Suhr H, Zeeh B (1968) Studies on diazomethanes
XXVI isodiazomethan = knallsäureamid = N-isocyanamin. Justus Liebigs Ann Chem 713:87–
95
77. Müller E, Beutler R, Zeeh B (1968) Studies on diazomethane XXVIII bang acid amide: the
double tautomer of diazomethane. Justus Liebigs Ann Chem 719:72–79
78. Beutler R, Zeeh B, Müller E (1969) Studies on diazomethanes XXIX. Reactions with the
tautomeric diazomethyl anion. Chem Ber 102:2636–2639
79. Boche G, Lohrenz JCW, Schubert F (1994) Lithio-diazomethane and lithio-(trimethylsilyl)
diazomethane: theoretical and experimental studies of their structures, reactions and reaction
products. Tetrahedron 50:5889–5902
80. Müller E, Rundel W (1956) Studies on diazomethanes VI: reaction of diazoethane with
methyllithium. Chem Ber 89:1065–1071
81. Baceiredo A, Igau A, Bertrand G, Menu MJ, Dartiguenave Y, Bonnet JJ (1986)
Phosphinocarbene-phosphaalkene rearrangement and intramolecular wittig-like reaction
involving a phosphorus vinyl ylide. J Am Chem Soc 108:7868–7869
82. Menu MJ, Crocco G, Dartiguenave M, Dartiguenave Y, Bertrand G (1988) Reactivity
of Rh(PMe 3 ) 4 Cl with lithium derivatives of phosphorus-substituted diazomethanes. First
evidence for a transient nitrogen-transition-metal nitrile imine. X-ray structure of [cyclic]
(PMe 3 ) 2 RhNBuNCHP (N-iso-Pr 2 ) 2 . Organometallics 7:2231–2233
83. Boche G, Harms K, Marsch M, Schubert F (1994) {6 Lithio(trimethylsilyl)diazomethane 2
Lithio[4,5-bis(trimethylsilyl)triazene]·7 Diethyl Ether}: the first X-ray structure analysis of a
lithiated diazoalkane. Chem Ber 127:2193–2195
84. Reau R, Veneziani G, Bertrand G (1992) Formation of nitrilimines and diazo compounds from
lithiated and stannyl diazo derivatives: scope and mechanism. J Am Chem Soc 114:6059–6063
85. Castan F, Baceiredo A, Bertrand G (1989) A distillable C- and N-silylated nitrile imine. Angew
Chemie Int Ed English 28:1250–1251
86. Arthur MP, Goodwin HP, Baceiredo A, Dillon KB, Bertrand G (1991) Synthesis of stable
boryl-substituted diazomethane and nitrilimines. Organometallics 10:3205–3210
87. Chu J, Kefalidis CE, Maron L, Leng X, Chen Y (2013) Chameleon behavior of a newly
synthesized scandium nitrilimine derivative. J Am Chem Soc 135:8165–8168
1 Nitrile Imines and Their Properties
65. Castan F, Baceiredo A, Bigg D, Bertrand G (1991) Synthesis and reactivity of stable silylsubstituted nitrilimines. J Org Chem 56:1801–1807
66. Bertrand G, Wentrup C (1994) Nitrile imines: from matrix characterization to stable
compounds. Angew Chemie Int Ed English 33:527–545
67. Leue C, Reau R, Neumann B, Stammler H-G, Jutzi P, Bertrand G (1994) Preparation of monoand bis(germyl) nitrilimines from germylenes and stannyl diazo derivatives. Organometallics
13:436–438
68. Sicard G, Baceiredo A, Bertrand G (1988) Synthesis and reactivity of a stable nitrile imine. J
Am Chem Soc 110:2663–2664
69. Müller E, Disselhoff H (1933) Über die Einwirkung von natrium auf aliphatische
diazoverbindungen. Naturwissenschaften 21:661
70. Müller E, Disselhoff H (1934) Studies on diazomethanes I. Justus Liebig’s Ann der Chemie
512:250–263
71. Müller E, Kreutzmann W (1934) Studies on diazomethanes II. Justus Liebig’s Ann der Chemie
512:264–275
72. Müller E, Ludsteck D (1954) Studies on diazomethanes III: preparation of isodiazomethane
and its rearrangement to diazomethane. Chem Ber 87:1887–1895
73. Müller E, Ludsteck D (1955) Studies on diazomethanes V: reactive behavior of
diazomethyllithium. Chem Ber 88:921–933
74. Müller E, Rundel W (1957) Studeis on diazomethanes IX. Another recent synthesis of
diazomethane and isodiazomethane. Chem Ber 90:2673–2678
75. Müller E, Kästner P, Rundel W (1965) Studies on diazomethanes XXII: The structure of
isodiazomethane. Chem Ber 98:711–714
76. Müller E, Kästner P, Beutler R, Rundel W, Suhr H, Zeeh B (1968) Studies on diazomethanes
XXVI isodiazomethan = knallsäureamid = N-isocyanamin. Justus Liebigs Ann Chem 713:87–
95
77. Müller E, Beutler R, Zeeh B (1968) Studies on diazomethane XXVIII bang acid amide: the
double tautomer of diazomethane. Justus Liebigs Ann Chem 719:72–79
78. Beutler R, Zeeh B, Müller E (1969) Studies on diazomethanes XXIX. Reactions with the
tautomeric diazomethyl anion. Chem Ber 102:2636–2639
79. Boche G, Lohrenz JCW, Schubert F (1994) Lithio-diazomethane and lithio-(trimethylsilyl)
diazomethane: theoretical and experimental studies of their structures, reactions and reaction
products. Tetrahedron 50:5889–5902
80. Müller E, Rundel W (1956) Studies on diazomethanes VI: reaction of diazoethane with
methyllithium. Chem Ber 89:1065–1071
81. Baceiredo A, Igau A, Bertrand G, Menu MJ, Dartiguenave Y, Bonnet JJ (1986)
Phosphinocarbene-phosphaalkene rearrangement and intramolecular wittig-like reaction
involving a phosphorus vinyl ylide. J Am Chem Soc 108:7868–7869
82. Menu MJ, Crocco G, Dartiguenave M, Dartiguenave Y, Bertrand G (1988) Reactivity
of Rh(PMe 3 ) 4 Cl with lithium derivatives of phosphorus-substituted diazomethanes. First
evidence for a transient nitrogen-transition-metal nitrile imine. X-ray structure of [cyclic]
(PMe 3 ) 2 RhNBuNCHP (N-iso-Pr 2 ) 2 . Organometallics 7:2231–2233
83. Boche G, Harms K, Marsch M, Schubert F (1994) {6 Lithio(trimethylsilyl)diazomethane 2
Lithio[4,5-bis(trimethylsilyl)triazene]·7 Diethyl Ether}: the first X-ray structure analysis of a
lithiated diazoalkane. Chem Ber 127:2193–2195
84. Reau R, Veneziani G, Bertrand G (1992) Formation of nitrilimines and diazo compounds from
lithiated and stannyl diazo derivatives: scope and mechanism. J Am Chem Soc 114:6059–6063
85. Castan F, Baceiredo A, Bertrand G (1989) A distillable C- and N-silylated nitrile imine. Angew
Chemie Int Ed English 28:1250–1251
86. Arthur MP, Goodwin HP, Baceiredo A, Dillon KB, Bertrand G (1991) Synthesis of stable
boryl-substituted diazomethane and nitrilimines. Organometallics 10:3205–3210
87. Chu J, Kefalidis CE, Maron L, Leng X, Chen Y (2013) Chameleon behavior of a newly
synthesized scandium nitrilimine derivative. J Am Chem Soc 135:8165–8168