Heavier group 2 grignard reagents of the type Aryl-Ae(L) n -X (Post-Grignard Reagents)

Topics in Organometallic Chemistry

Volumn 45, Issue , 2013, Pages 29-72

  Westerhausen, Matthias ^a   Langer, Jens ^a   Krieck, Sven ^a   Fischer, Reinald ^a   Görls, Helmar ^a   Köhler, Mathias ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Arylcalcium; Calcium; Diarylcalcium; Ether degradation; Organylcalcium; Post grignard reagents

Indexed keywords

EID: 84881322357     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-3-642-36270-5_2     Document Type: Review

References (166)

1. Seyferth D (2009) The Grignard reagents. Organometallics 28:1598-1605
2. Bickelhaupt F (1994) Organomagnesium chemistry: Nearly hundred years but still fascinating. J Organomet Chem 475:1-14
3. Walborsky HM (1990) Mechanism of Grignard reagent formation. The surface nature of the reaction. Acc Chem Res 23:286-293
4. Walborsky HM (1991) Wie entsteht eine Grignard-Verbindung? Chemie in unserer Zeit 25:108-116
5. Walborsky HM, Zimmermann C (1992) The surface nature of Grignard reagent formation. Cyclopropylmagnesium bromide. J Am Chem Soc 114:4996-5000
6. Garst JF (1991) Grignard reagent formation and freely diffusing radical intermediates. Acc Chem Res 24:95-97
7. Garst JF, Ungváry F (2000) Mechanisms of Grignard reagent formation. In: Richey HG Jr (ed) Grignard reagents: New developments, Chap. 7. Wiley, Chichester, pp 185-275
8. Garst JF, Soriaga MP (2004) Grignard reagent formation. Coord Chem Rev 248:623-652
9. Richey HG Jr (2000) Grignard reagents: New developments. Wiley, Chichester
10. Wakefield BJ (1995) Organomagnesium methods in organic synthesis. Academic, London
11. Rappoport Z, Marek I (2008) The chemistry of organomagnesium compounds (Patai Series: The chemistry of functional groups). Wiley, Chichester
12. Schlosser M (1973) Struktur und Reaktivität polarer Organometalle: Eine Einführung in die Chemie organischer Alkali- und Erdalkalimetall- Verbindungen. Springer, Heidelberg
13. Schlenk W, Schlenk W (1929) Über die Konstitution der Grignardschen Magnesiumverbindungen. Chem Ber 62:920-924
14. Heard PJ (2008) NMR of organomagnesium compounds. In: Rappoport Z, Marek I (eds) The chemistry of organomagnesium compounds (Patai Series: The chemistry of functional groups), Chap. 3. Wiley, Chichester, pp 131-154
15. Yamabe S, Yamazaki S (2008) Theoretical studies of the addition of RMgX to carbonyl compounds. In: Rappoport Z, Marek I (eds) The chemistry of organomagnesium compounds (Patai Series: The chemistry of functional groups), Chap. 9. Wiley, Chichester, pp 369-402
16. Liebman JF, Holm T (2008) The thermochemistry of organomagnesium compounds. In: Rappoport Z, Marek I (eds) The chemistry of organomagnesium compounds (Patai Series: The chemistry of functional groups), Chap. 2. Wiley, Chichester, pp 101-129
17. Garst JF, Lawrence KE, Batlaw R, Boone JR, Ungváry F (1994) Magnesium bromide in Grignard reagent formation. Inorg Chim Acta 222:365-375
18. Langer J, Krieck S, Fischer R, Görls H, Walther D, Westerhausen M (2009) 1,4-Dioxane adducts of bis(2,4,6-trimethylphenyl)magnesium: Synthesis, ether cleavage reactions, and structural diversity of Grignard reagent/1,4-dioxane complexes. Organometallics 28:5814-5820
19. Markies PR, Akkerman OS, Bickelhaupt F, Smeets WJJ, Spek AL (1991) X-ray structural analyses of organomagnesium compounds. Adv Organomet Chem 32:147-226
20. Holloway CE, Melnik M (1994) Magnesium compounds: Classification and analysis of crystallographic and structural data. J Organomet Chem 465:1-63
21. Bickelhaupt F (2000) Structures of organomagnesium compounds as revealed by X-ray diffraction studies. In: Richey HG Jr (ed) Grignard reagents: New developments, Chap. 9. Wiley, Chichester, pp 299-328
22. Jastrzebski JTBH, Boersma J, van Koten G (2008) Structural organomagnesium chemistry. In: Rappoport Z, Marek I (eds) The chemistry of organomagnesium compounds (Patai Series: The chemistry of functional groups), Chap. 1. Wiley, Chichester, pp 1-99
23. Stucky G, Rundle RE (1964) The constitution of the Grignard reagent, phenylmagnesium bromide dietherate. J Am Chem Soc 86:4825-4830
24. 4. Chem Ber 102:2035-2043.
25. 8O J Organomet Chem 20:1-10
26. Yousef RI, Walfort B, Rüffer T, Wagner C, Schmidt H, Herzog R, Steinborn D (2005) Synthesis, characterization and Schlenk equilibrium studies of methylmagnesium compounds with O- And N-donor ligands - the unexpected behavior of [MgMeBr(pmdta)] (pmdta N,N, N',N",N"- pentamethyldiethylenetriamine). J Organomet Chem 690:1178-1191
27. Vestergren M, Eriksson J, Ha°kansson M (2003) Absolute asymmetric synthesis of "chiral-atmetal" Grignard reagents and transfer of the chirality to carbon. Chem Eur J 9:4678-4686
28. 2 a tetrameric Grignard reagent J Organomet Chem 28:5-20
29. Sakamoto S, Imamoto T, Yamaguchi K (2001) Constitution of Grignard reagent RMgCl in tetrahydrofuran. Org Lett 3:1793-1795
30. 3. J Organomet Chem 469:129-133.
31. 2-) Organometallics 14:3264-3267.
32. 3] Organometallics 11:3209-3214
33. Markies PR, Schat G, Akkerman OS, Bickelhaupt F, Smeets WJJ, van der Sluis P, Spek AL (1990) The coordination modes of simple diarylmagnesium species: some representative X-ray crystal structures. J Organomet Chem 393:315-331
34. Weiss E (1964) Die Kristallstruktur des Dimethylmagnesiums. J Organomet Chem 2:314-321
35. Weiss E (1965) Die Kristallstruktur des Diäthylmagnesiums. J Organomet Chem 4:101-108
36. Wehmschulte RJ, Twamley B, Khan MA (2001) Synthesis and characterization of an unsolvated dimeric diarylmagnesium compound and ist magnesium iodide byproducts. Inorg Chem 40:6004-6008
37. Parvez M, Pajerski AD, Richey HG Jr (1988) (Dioxane)dineopentylmagnesium: a polymeric structure. Acta Cryst C44:1212-1215
38. 2Zr(ethene) L)] (L THF, pyridine), and [(indenyl)2Zr(ethene)(THF)] and of metallacycles with norbornene Organometallics 19:2532-2540
39. Markies PR, Akkerman OS, Bickelhaupt F, Smeets WJJ, Spek AL (1994) Complexation of bis(p-tert-butylphenyl)magnesium with xylylene crown ethers and glymes. Organometallics 13:2616-2627
40. Markies PR, Nomoto T, Akkerman OS, Bickelhaupt F (1988) X-ray structure of (1,3-xylyl-18-crown-5)diphenylmagnesium: an organometallic rotaxane. J Am Chem Soc 110:4845-4846
41. Mulvey RE (2001) s-Block metal inverse crowns: synthetic and structural synergism in mixed alkali metal-magnesium (or zinc) amide chemistry. Chem Commun:1049-1056
42. Mulvey RE, Mongin F, Uchiyama M, Kondo Y (2007) Deprotonative metalation using ate compounds: synergy, synthesis, and structure building. Angew Chem Int Ed 46:3802-3824, Angew Chem 119:3876-3899
43. Yorimitsu H, Oshima K (2008) The chemistry of organomagnesium ate complexes. In: Rappoport Z, Marek I (eds) The chemistry of organomagnesium compounds (Patai Series: The chemistry of functional groups), chap 15. Wiley, Chichester, pp 681-715
44. Knochel P, Gavryushin A, Brade K (2008) Functionalized organomagnesium compounds: Synthesis and reactivity. In: Rappoport Z, Marek I (eds) The chemistry of organomagnesium compounds (Patai Series: The chemistry of functional groups), chap 12. Wiley, Chichester, pp 511-593
45. Ackermann L, Althammer A (2009) Moderne Magnesiumorganische Chemie. Chemie in unserer Zeit 43:74-83
46. Lappert M.F.,Power P.P.,Sanger A.R.,Srivastava R.C. 1980 Metal and Metalloid Amides 45-67 chap 3 Ellis Horwood, Chichester
47. Lappert M, Protchenko A, Power PP, Seeber A (2009) Metal amide chemistry, chap 3,p 39-78. Wiley, Chichester
48. Hull KL, Henderson KW (2008) Organomagnesium-group 15-and organomagnesium-group 16-bonded complexes. In: Rappoport Z, Marek I (eds) The chemistry of organomagnesium compounds (Patai Series: The chemistry of functional groups), chap 10. Wiley, Chichester, p 403-36
49. Westerhausen M, Langer J, Krieck S, Glock C (2011) Calcium-based organometallics and superbases - Alkyl-, aryl-, and amidocalcium compounds. Rev Inorg Chem 31:143-184
50. Mulvey RE (2009) Avant-garde metalating agents: Structural basis of alkali-metal-mediated metalation. Acc Chem Res 42:743-755
51. Stephan DW, Erker G (2010) Frustrated Lewis pairs: Metal-free hydrogen activation and more. Angew Chem Int Ed 49:46-76, Angew Chem 122:50-81
52. Jaric M, Haag BA, Unsinn A, Karaghiosoff K, Knochel P (2010) Highly selective metalations of pyridines and related heterocycles using frustrated Lewis pairs of tmp-zinc and tmpmagnesium bases with BF3•OEt2. Angew Chem Int Ed 49:5451-5455, Angew Chem 122:5582-5586
53. Beckmann E (1905) Einige Anwendungen von metallischem Calcium. Ber Dtsch Chem Ges 38:904-906
54. Gilman H, Schulze F (1926) Organocalcium Iodides. J Am Chem Soc 48:2463-2467
55. Bryce-Smith D, Skinner AC (1963) Organometallic compounds of Group II. Part IV. Preparation and reactions of organocalcium halides. J Chem Soc:577-585
56. Markies PR, Nomoto T, Schat G, Akkerman OS, Bickelhaupt F (1991) UnusualMetalation and Halogen-Metal Exchange Reactions between 1,3-Xylyl Crown Ethers and Organomagnesium Reagents. X-ray Structure of 2-[(p-tert-Butylphenyl) magnesio]-1,3-xylylene-18-crown-5. Organometallics 10:3826-3837
57. Gilman H, Kirby RH (1941) Addition Reactions of Organometallic Compounds with Conjugated Systems. J Am Chem Soc 63:2046-2048
58. Fraenkel G, Dayagi S, Kobayashi S (1968) Nuclear Magnetic Resonance and Ultraviolet Spectroscopy of Substituted Aromatic Organometallic Compounds of Lithium, Magnesium, and Calcium. J Phys Chem 72:953-961
59. Kawabata N, Matsumura A, Yamashita S (1973) Preparation of Organocalcium Halides. Tetrahedron 29:1069-1071
60. Kawabata N, Matsumura A, Yamashita S (1973) Preparation of Organocalcium Halides in Hydrocarbon Solvents. J Org Chem 38:4268-4270
61. x Influence of Alkali-Metal Cations on Ligand Exchange Reactions Organometallics 19:1556-1566
62. Kawabata N, Matsumura A, Yamashita S (1973) Reactions of methylcalcium iodide. J Org Chem 38:3403-3406
63. Evers J, Weiss A, Kaldis E, Muheim J (1973) Purification of calcium and barium by reactive distillation. J Less-Common Met 30:83-95
64. Kaldis E, Muheim J, Evers J,Weiss A (1973) Purification of strontium by reactive distillation. J Less-Common Met 31:169-173
65. Suslick KS (1986) Organometallic Sonochemistry. Adv Organomet Chem 25:73-119
66. 2Ca type. Zh Obshch Khim 42:841-843
67. 2Ca type. Dokl Akad Nauk SSSR 210:1134-1135
68. 2Ca-type organocalcium compounds and their complexes. Zh Obshch Khim 44:1135-1137
69. Mochida K, Ogawa H (1983) Preparation and reactions of solvent-free arylcalcium halides ArCaX (X F, Cl, Br). J Organomet Chem 243:131-135
70. Mochida K, Yamanishi T (1987) A new method for preparation of organocalcium halides by cocondensation of calcium vapor with solvents. J Organomet Chem 332:247-252
71. 2 J Chem Soc, Chem Commun:724-726
72. Klabunde KJ (1975) Organic chemistry of metal vapors. Acc Chem Res 8:393-399
73. Johnson WC, Strubbs MF, Sidwell AE, Pechukas A (1939) The rate of formation and the dissociation of calcium hydride. J Am Chem Soc 61:318-329
74. Utke AR, Sanderson RT (1964) Reactions of calcium with organonitrogen compounds and aromatic hydrocarbons. J Org Chem 29:1261-1264
75. Drake SR, Otway DJ (1991) The synthesis of metal organic compounds of calcium, strontium and barium by ammonia gas-saturated ethereal solvents. J Chem Soc, Chem Commun:517-519, Erratum: Drake SR, Otway DJ (1991) Corrigendum. J Chem Soc, Chem Commun:1060
76. Fischer R, Gärtner M, Görls H, Westerhausen M (2006) Synthesis and spectroscopic properties of arylcalcium halides. Organometallics 25:3496-3500
77. Biltz W, Hüttig GF (1920) Beiträge zur systematischen Verwandtschaftslehre. XII: Über die Verbindungen von Ammoniak mit metallischem Calcium, Strontium und Barium. Z Anorg Allg Chem 114:241-265
78. Wu T-C, Xiong H, Rieke RD (1990) Organocalcium chemistry: preparation and reactions of highly reactive calcium. J Org Chem 55:5045-5051
79. Rieke RD (1989) Preparation of organometallic compounds from highly reactive metal powders. Science 246:1260-1264
80. McCormick MJ, Moon KB, Jones SR, Hanusa TP (1990) Preparation of activated calcium, strontium, and barium powders by reduction of alkaline earth di-iodides. J Chem Soc, Chem Commun:778-779
81. Fürstner A (1993) Chemistry of and with highly reactive metals. Angew Chem Int Ed 32:164-190, Angew Chem 105:171-197
82. Bogdanović B, Liao S-T, Mynott R, Schlichte K, Westeppe U (1984) Rate of formation and characterization of magnesium anthracene. Chem Ber 117:1378-1392
83. Bogdanović B, Janke N, Kinzelmann H-G, Westeppe U (1988) Neue Magnesiumanthracen-Komplexe durch Ligandenaustausch. Chem Ber 121:33-37
84. Gärtner M, Görls H, Westerhausen M (2007) Synthesis of arylcalcium halides - general procedure, scope and limitations. Synthesis:725-730
85. Glaunsinger WS, White TR, von Dreele RB, Gordon DA, Marzke RF, Bowman AL, Yarnell JL (1978) Structures and molecular motions in alkaline earth hexammines. Nature 271:414-417
86. Damay P, Leclercq F, Chieux P (1990) Geometry of the ND3 group in a metallic Ca(ND3)6 compound and in solid and liquid deuteroammonia as measured by neutron scattering. Phys Rev B 41:9676-9682
87. Westerhausen M (2001) 100 Years after Grignard: Where does the organometallic chemistry of the heavy alkaline earth metals stand today? Angew Chem Int Ed 40:2975-2977, Angew Chem 113:3063-3065
88. Masthoff R, Schüler H, Krieg G (1968)Über Organometallverbindungen der II. Hauptgruppe VI Synthese und Eigenschaften von Triphenylmethylcalcium-chlorid-Donor-Akzeptorkomplexen J Organomet Chem 13:37-43
89. Westerhausen M, Gärtner M, Fischer R, Langer J (2007) Arylcalcium compounds: Syntheses, structures, physical properties, and chemical behaviour. Angew Chem Int Ed 46:1950-1956, Angew Chem 119:1994-2001
90. Westerhausen M, Gärtner M, Fischer R, Langer J, Yu L, Reiher M (2007) Heavy Grignard reagents: Challenges and possibilities of aryl alkaline earth metal compounds. Chem Eur J 13:6292-6306
91. Westerhausen M (2008) Heavy Grignard reagents - synthesis and reactivity of organocalcium compounds. Coord Chem Rev 252:1516-1531
92. Westerhausen M (2009) Recent developments in organic chemistry of calcium - An element with unlimited possibilities in organometallic chemistry? Z Anorg Allg Chem 635:13-32
93. 2] Z Anorg Allg Chem 636:1190-1198
94. 4I with potassium compounds. Organometallics 26:1077-1083
95. Langer J, Görls H, Westerhausen M (2007) Phenylcalcium iodides with silyl substituents in para-position. Inorg Chem Commun 10:853-855
96. Fischer R, Gärtner M, Görls H, Westerhausen M (2006) Synthesis of 2,4,6- trimethylphenylcalcium iodide and degradation in THF solution. Angew Chem Int Ed 45:609-612, Angew Chem 118:624-627
97. Fischer R, Gärtner M, Görls H, Yu L, Reiher M, Westerhausen M (2007) THF solvates of extremely soluble bis(2,4,6-trimethylphenyl)calcium and tris(2,6-dimethoxyphenyl) dicalcium iodide. Angew Chem Int Ed 46:1618-1623, Angew Chem 119:1642-1647
98. 3] and stability of aryl-substituted phenylcalcium complexes. J Am Chem Soc 132:12492-12501.
99. Gärtner M, Görls H, WesterhausenM(2008) Synthesis and derivatization of naphthylcalcium halides as well as degradation in THF solution. J Organomet Chem 693:221-227
100. 3]. J Am Chem Soc 131:2977-2985
101. Bloomfield PR (1959) Improvements in or relating to the preparation of organic lithium compounds. Brit Patent 904456
102. Rieke RD, Bales SE (1973) Activated metals. The effect of added metal salts on magnesium reactivity. J Chem Soc, Chem Commun:879-880
103. Bruhat G, Thomas V (1926) The dimagnesium derivatives of benzene. Compt rend 183:297-299
104. Langer J, Görls H, Westerhausen M (2010) Stability and reactivity of phenylstrontium compounds in solution. Organometallics 29:2034-2039
105. 5 pyramid. Inorg Chem Commun 10:1001-1004
106. Langer J, Krieck S, Görls H, Westerhausen M (2009) An efficient general synthesis of halide-free diarylcalcium. Angew Chem Int Ed 48:5741-5744, Angew Chem 121:5851-5854
107. Hauber S-O, Lissner F, Deacon GB, Niemeyer M (2005) Stabilization of aryl-calcium, -strontium, and -barium compounds by designed steric and π-bonding encapsulation. Angew Chem Int Ed 44:5871-5875, Angew Chem 117: 6021-6025
108. 3]+ [Ph-Cu-Ph]. Organometallics 26:3269-3271
109. Langer J, Krieck S, Görls H, Kreisel G, Seidel W, Westerhausen M (2010) Organic heterobimetallic complexes of the alkaline-earth metals (Ae Ca, Sr, Ba) with tetrahedral metallate anions of three-valent metals (M B, Al, Ga, and V). New J Chem 34:1667-1677
110. Krieck S, Görls H, Westerhausen M (2010) Structural diversity of calcium cuprates via addition and transmetalation reactions of mesity copper(I). Chem Asian J 5:272-277
111. Harder S,Müller S, Hübner E (2004) Syntheses and crystal structures of simple dibenzylcalcium complexes: Useful reagents in the preparation of calcium compounds. Organometallics 23:178-183
112. Ruspic C, Harder S (2005) Synthesis and structure of an arylcalcium compound with an unusual calcium tetrahedron containing an encapsulated oxide. Organometallics 24:5506-5508
113. Fischer R, Langer J, Krieck S, Görls H, Westerhausen M (2011) Coordination behaviour of calcocene and its use as a synthon for heteroleptic organocalcium compounds. Organometallics 30:1359-1365
114. Gowenlock BG, Lindsell WE (1977) The organometallic chemistry of the alkaline-earth metals. J Organomet Chem Libr, Organomet Chem Rev 3:1-73
115. Lindsell WE (1982) Calcium, strontium and barium. In: Wilkinson G, Stone FGA, Abel EW (eds) Comprehensive organometallic chemistry - the synthesis, reactions and structures of organometallic compounds, vol 1. Pergamon Press, New York, NY, pp 237-252, Chap. 4.2.4
116. Reich HJ, Green DP, Medina MA, Goldenberg WS, Gudmundsson BÖ, Dykstra RR, Phillips NH (1998) Aggregation and reactivity of phenyllithium solutions. J Am Chem Soc 120:7201-7210
117. Hesse M, Meier H, Zech B (2005) Spektroskpische Methoden in der organischen Chemie. Thieme, Stuttgart
118. Gärtner M, Fischer R, Langer J, Görls H, Walther D, Westerhausen M (2007) Syntheses and structures of alkaline-earth metal bis(diphenylamides). Inorg Chem 46:5118-5124
119. Gillespie RJ, Silvi B (2002) The octet rule and hypervalence: Two misunderstood concepts. Coord Chem Rev 233-234:53-62
120. Gillespie RJ (1992) The VSEPR model revisited. Chem Soc Rev 21:59-69
121. Gillespie RJ (2008) Fifty years of the VSEPR model. Coord Chem Rev 252:1315-1327, and literature cited therein
122. 2- Angew Chem Int Ed Engl 33:1257-1259, Angew Chem 106:1364-1365
123. Krieck S, Görls H, Westerhausen M (2010) Synthesis and characterization of rare examples of stable potassium and arylcalcium triethylboranate complexes. Inorg Chem Commun 13:1466-1469
124. Dell'Amico DB, Bradicich C, Labella L, Marchetti F (2006) Complexes of calcium halides with 1,2-dimethoxyethane (DME). Inorg Chim Acta 359:1659-1665
125. Henderson KW, Rood JA, Noll BC (2005) A low-temperature investigation of trans-diiodotetrakis (tetrahydrofuran)calcium(II). Acta Cryst E61:m2006-m2007
126. 2O:O0)diiodo (tetrahydrofuran-κO) calcium(II). Acta Cryst E63:m3169
127. 2. Chem Commun:1961-1962
128. Crimmin MR, Barrett AGM, Hill MS, MacDougall DJ, Mahon MF, Procopiou PA (2008) Bis (trimethylsilyl)methyl derivatives of calcium, strontium and barium: Potentially useful dialkyls of the heavy alkaline-earth elements. Chem Eur J 14:11292-11295
129. Orzechowski L, Harder S (2007) Isolation of an intermediate in the catalytic trimerization of isocyanates by a monomeric calcium carbine with chelating iminophosphorane substituents. Organometallics 26:2144-2148
130. Kottke T, Stalke D (1993) Crystal handling at low temperatures. J Appl Cryst 26:615-619
131. Stalke D (1998) Cryo crystal structure determination and application to intermediates. Chem Soc Rev 27:171-178
132. Harder S (2010) From Limestone to Catalysis: Application of Calcium Compounds as Homogeneous Catalysts. Chem Rev 110:3852-3876
133. Barrett AGM, Crimmin MR, Hill MS, Procopiou PA (2010) Heterofunctionalization Catalysis with Organometallic Compounds of Calcium, Strontium and Barium. Proc R Soc 466:927-963
134. Westerhausen M (2006) Recent developments in the field of organic heterobimetallic compounds of the alkaline-earth metals. Dalton Trans:4755-4768
135. Krieck S, Görls H, Westerhausen M (2008) Synthesis and properties of calcium tetraorganylalanates with [Me4-nAlPhn]- Anions. Organometallics 27:5052-5057
136. Billups WE, Konarski MM, Hauge RH, Margrave JL (1980) Carbon-carbon bond formation in the reaction of calcium atoms with ethers. J Am Chem Soc 102:3649-3650
137. Maercker A (1987) Ether cleavage with organo-alkali-metal compounds and alkali metals. Angew Chem Int Ed Engl 26:972-989, Angew Chem 99:1002-1019
138. Stanetty P, Mihovilovic MD (1997) Half-lives of organolithium reagents in common etheral solvents. J Org Chem 62:1514-1515
139. 2•(thf) CaO] with a central Ca4 tetrahedron. Inorg Chem Commun 8:1159-1161
140. 2]. J Organomet Chem 694:2204-2209
141. Westerhausen M, Schwarz W (1992) Calcium-bis[N, N'-bis(trimethylsilyl) benzamidinat]- THF (1/2) - Synthese, specktroskopische Charakterisierung und Struktur. Z Naturforsch 47b:453-459
142. Setzer WN, Schleyer PvR (1985) X-ray structural analyses of organolithium compounds. Adv Organomet Chem 24:353-451
143. Weiss E (1993) Structures of organo alkali metal complexes and related compounds. Angew Chem Int Ed Engl 32:1501-1523, Angew Chem 105:1565-1587
144. Stey T, Stalke D (2004) Lead structures in lithium organic chemistry. In: Rappoport Z, Marek I (eds) The chemistry of organolithium compounds (Patai Series: The Chemistry of functional groups), chap 2. Wiley, Chichester, pp 47-120
145. Gessner VH, Däschlein C, Strohmann C (2009) Structure formation principles and reactivity of organolithium compounds. Chem Eur J 15:3320-3334
146. Ritter SK (2011) Calcium's awakening. Chem Eng News 89(10):49-51
147. Green SP, Jones C, Stasch A (2007) Stable magnesium(I) compounds with Mg-Mg bonds. Science 318:1754-1757
148. Stach A, Jones C (2011) Dalton Trans 40:5659-5672
149. Westerhausen M (2008) Molecular magnesium(I) compounds - from curiosity to kudos. Angew Chem Int Ed 47:2185-2187, Angew Chem 120:2215-2217
150. Krieck S, WesterhausenM(2009) Subvalenz bei elektropositiven s-Block-Metallen. Chem in unserer Z 43:384-390
151. Krieck S, Yu L, Reiher M, Westerhausen M (2010) Subvalent organometallic compounds of the alkaline-earth metals in low oxidation states. Eur J Inorg Chem:197-216
152. Jutzi P (1986) π-Bonding to main group elements. Adv Organomet Chem 26:217-295
153. Jutzi P (1990) Cyclopentadienyl complexes with main group elements as central atoms - A decade of research. J Organomet Chem 400:1-17
154. Hanusa TP (1990) New developments in the organometallic chemistry of calcium, strontium and barium. Polyhedron 9:1345-1362
155. Hanusa TP (1993) Ligand influences on structure and reactivity in organoalkaline-earth chemistry. Chem Rev 93:1023-1036
156. Burkey DJ, Hanusa TP (1995) Structural lessons from main-group metallocenes. Comments Inorg Chem 17:41-77
157. Hays ML, Hanusa TP (1996) Substituent effects as probes of structure and bonding in mononuclear metallocenes. Adv Organomet Chem 40:117-170
158. Jutzi P, Burford N (1999) Structurally diverse π-cyclopentadienyl complexes of the main group elements. Chem Rev 99:969-990
159. Hanusa TP (2002) New developments in the cyclopentadienyl chemistry of the alkaline- earth metals. Organometallics 21:2559-2571
160. 2 Organometallics 15:4971-4976
161. Green DC, Englich U, Ruhlandt-Senge K (1999) Calcium, strontium, and barium acetylides - new evidence for bending in the structures of heavy alkaline-earth metal derivatives. Angew Chem Int Ed 38:354-357, Angew Chem 111:365-367
162. Barrett AGM, Crimmin MR, Hill MS, Hitchcock PB, Lomas SL, Mahon MF, Procopiou PA, Suntharalingam K (2008) β-Diketiminato calcium acetylides: Synthesis, solution dimerization, and catalytic carbon-carbon bond formation. Organometallics 27:6300-6306
163. Feil F, Harder S (2000) α, α-Bis(trimethylsilyl)-substituted benzyl complexes of potassium and calcium. Organometallics 19:5010-5015
164. Harder S, Feil F, Weeber A (2001) Structure of a benzylcalcium diastereomer: An initiator for the anionic polymerization of styrene Organometallics 20:1044-1046
165. Feil F, Müller C, Harder S (2003) α-Methyl-benzylcalcium complexes: Syntheses, structures and reactivity. J Organomet Chem 683:56-63
166. Guino-o MA, Campana CF, Ruhlandt-Senge K (2008) A unique heterobimetallic benzyl calciate - An organometallic mixed-metal species involving a heavy alkaline-earth metal. Chem Commun:1692-1694