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Organometallics

Volumn 26, Issue 16, 2007, Pages 4076-4079

Reactions of β-diketiminate-stabilized calcium amides with 9-borabicyclo[3.3.1]nonane (9-BBN)

(5) Barrett, Anthony G M a Crimmin, Mark R a Hill, Michael S a Hitchcock, Peter B b Procopiou, Panayiotis A c

a IMPERIAL COLLEGE LONDON (United Kingdom)

b UNIVERSITY OF SUSSEX (United Kingdom)

c GLAXOSMITHKLINE (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM COMPOUNDS; CHEMICAL BONDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

BOND METATHESIS MECHANISMS; CALCIUM AMIDES; REACTION COPRODUCTS;

ORGANOMETALLICS;

EID: 34547819187 PISSN: 02767333 EISSN: None Source Type: Journal
DOI: 10.1021/om070083t Document Type: Article

Times cited : (46)

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- Reaction of 1 with 9-BBN: a stirred solution of 1 (500 mg, 0.74 mmol) and 9-BBN dimer (244 mg, 0.74 mmol) in toluene (10 mL) was heated to 60°C for 2 h. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. The crude product was then extracted into hexane and the extract filtered. Slow removal of the solvent induced crystallization, and the product 3 was isolated as a white crystalline solid (116 mg, 0.178 mmol, 24, Mp (hexane, 135°C dec. 1H NMR (dg-tol, 400 MHz, 298 K, δ, 0.67 (broad singlet, 2H, 1.14 (d, 12H, J, 6.8 Hz, 1.25 (d, 12H, J, 6.8 Hz, 1.28 (m, 4H, 1.48-1.60 (m, 4 H, 1.57 (s, 6H, 1.70-1.78 (m, 4 H, 1.86-1.96 (m, 4 H, 3.06 (hept, 4H, J, 6.8 Hz, 3.64 (m, 4H, 4.67 (s, 1H, 6.97-7.07 (m, 6H, 13C NMR (d 8-tol, 100 MHz, 298 K, δ, 24.3, 24.5 broad signal, 25.0, 25.3, 26.0, 28.6, 34.6, 69.8, 93.4, 123.2, 137.4, 141.5, 145.4, 166.2
- 2O: C, 75.52; H, 9.88; N, 4.40. Calcd: C, 75.43; H, 10.00; N, 4.30. Yield based upon NMR analysis using tetrakis(trimethylsilyl)silane as an internal standard: 81%.

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- Reaction of 2 with 9-BBN: a solution of 2 (700 mg, 1.0 mmol) and 9-BBN dimer (1.0 mmol) in toluene was stirred for 1 h at room temperature. The crude product was then extracted intp hexane and the extract filtered. Slow removal of the solvent induced crystallization, and the product 3 was isolated as a colorless crystalline solid (132 mg, 0.20 mmol, 20, The solvent was removed from the filtrate, and the remaining crude product sublimed at 130°C and 4 × 10-1 mbar to yield the amidoborane 4 as a colorless crystalline solid (35 mg, 0.12 mmol, 12, This latter product is moisture sensitive and could not be purified by fractional crystallization, due to contamination by 3. Although 4 has been reported in the literature,21 no characterization data have been described. 1H NMR (C6D6, 400 MHz, 298 K, δ, 1.44 (m, 2H, 1.48-1.55 (m, 2H, 1.82-1.87 (m, 8H, 1.92-2.02 m, 2H, 6.91-6
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- The reaction of 1 with some alternative common group 13 hydrides proved unsuccessful. Thus, the reaction of 1 with BH3· OEt2 resulted in the isolation of a product in which the β-diketiminate ligand had undergone reduction by the borane complex see Figure S2, Supporting Information, These results demonstrate the fragility of the complex 1 as a model for developing a reaction chemistry of calcium and suggest the properties of the substrate are important for a selective a-bond metathesis reaction to occur. In this respect, it is likely that the bulky bicycloborane moiety acts to temper further reactivity by sterically encapsulating the reactive calcium center
- 2 resulted in the isolation of a product in which the β-diketiminate ligand had undergone reduction by the borane complex (see Figure S2, Supporting Information). These results demonstrate the fragility of the complex 1 as a model for developing a reaction chemistry of calcium and suggest the properties of the substrate are important for a selective a-bond metathesis reaction to occur. In this respect, it is likely that the bulky bicycloborane moiety acts to temper further reactivity by sterically encapsulating the reactive calcium center.

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