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1 article(s) from Fox, Falco

Silanediol versus chlorosilanol: hydrolyses and hydrogen-bonding catalyses with fenchole-based silanes

Falco Fox,
Jörg M. Neudörfl and
Bernd Goldfuss

Beilstein J. Org. Chem. 2019, 15, 167–186, doi:10.3762/bjoc.15.17

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Graphical Abstract

Figure 1: Hydrogen-bonding silanediols, i.e., di(1-naphthyl)silanediol (1) [39], silanediols 2 [41-43], binaphthylsilane...

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Scheme 1: Hydrogen-bond-catalyzed N-acyl Mannich reaction of in situ-generated isoquinolin derivative 10 with...

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Scheme 2: Synthesis of BIFOXSiCl₂, starting with BIFOL (5) [52,54] yielding dichlorosilane 7.

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Scheme 3: Hydrolysis of BIFOXSiCl₂ (7) yielding the corresponding silanediol 9 and controlled hydrolysis of B...

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Scheme 4: Hydrolysis of dichlorosilanes 13 and 14 to their corresponding silanediols 1 and 15 [51,60].

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Figure 2: Hydrolyses of dichlorosilane 7 and 14 to BIFOXSi(OH)₂ (9, green circle) and bis(2,4,6-tri-tert-buty...

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Figure 3: Hydrolyses of BIFOXSiCl₂ (7) to BIFOXSi(OH)₂ (9, green circle), bis(2,4,6-tri-tert-butylphenoxy)dic...

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Scheme 5: Two investigated pathways for the hydrolysis of the dichlorosilanes. Front attack mechanism (front)...

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Figure 4: Three transition structures each, for the hydrolysis of BIFOXSiCl₂ (7) and BIFOXSiCl(OH) (8) consid...

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Figure 5: Computed hydrolyses of BIFOXSiCl₂ (7) to BIFOXSiCl(OH) 8_ax and BIFOXSiCl(OH) 8_eq and subsequent com...

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Figure 6: Transition state leading to 8_eq following front1 attack (E_a = 32.6 kcal mol⁻¹, Figure 5, Table 3, entry 1). Breaki...

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Figure 7: Transition state leading to 8_ax following front2 attack (E_a = 33.2 kcal mol⁻¹, Figure 5, Table 3, entry 2). Breaki...

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Figure 8: Transition state leading to 8_eq following side attack (E_a = 37.4 kcal mol⁻¹, Figure 5, Table 3, entry 3). Breaking...

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Figure 9: Transition state leading to 9 following side attack (E_a = 31.4 kcal mol⁻¹, Figure 5, Table 3, entry 6). Breaking a...

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Figure 10: Transition state leading to 9 following front1 attack (E_a = 33.4 kcal mol⁻¹, Figure 5, Table 3, entry 4). Breaking...

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Figure 11: Transition state leading to 9 following front2 attack (E_a = 40.2 kcal mol⁻¹, Figure 5, Table 3, entry 5). Breaking...

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Figure 12: X-ray crystal structure of BIFOXSiCl₂ (7). H atoms on the chiral backbone are omitted for clarity i...

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Figure 13: X-ray crystal structure of BIFOXSiCl(OH) (8). H atoms on the chiral backbone are omitted for clarit...

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Figure 14: X-ray crystal structure ofrac-BIFOXSi(OH)₂ (9) forming dimers. H atoms on the chiral backbone are o...

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Figure 15: X-ray crystal structure of BIFOXSi(OH)₂ (9) forming a tetramer. H atoms on the chiral backbone are ...

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Figure 16: X-ray crystal structure of BIFOXSi(OH)₂ (9) forming a dimeric structure with two bridged acetone mo...

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Figure 17: X-ray crystal structure of BIFOXSiCl(OH) (8), binding an acetone molecule. H atoms on the chiral ba...

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Scheme 6: Hydrogen-bond-catalyzed N-acyl Mannich reaction of in situ-generated 10 with different silyl ketene...

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Scheme 7: Hydrogen-bond-catalyzed nucleophilic substitution of 18 with BIFOXSi(OH)₂ (9) and nucleophile silyl...

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Scheme 8: Nucleophilic substitution of 20 with BIFOXSi(OH)₂ (9) and nucleophile silyl ketene acetals 11, 20 a...

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Published 18 Jan 2019

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