ChemInform Abstract: ELECTROCHEMICAL TRANSFORMATIONS OF STEROIDS

Ponsold, K.; Kasch, H.

doi:10.1002/chin.198236339

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2013

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“…Our first trial on the anodic cyanation of p-anisyltrimethylsilanes, which was easily prepared via the reaction of 4-bromomagnesiumanisole and chlorotrimethylsilane, gave predominantly a mixture of the direct-substituted product (2), in which a hydrogen atom was substituted with a cyano group, and the ipso-substituted product (3) in which the silyl group was substituted with a cyanide anion despite the presence of the bulky trimethylsilyl group (Scheme 1). 23 The substituents on the silyl group (1a and 1b) and the presence of different alkoxyl groups (1b and 1d) were important factors that influenced the selectivity and composition of the products, as shown in Table 1.…”

Section: Resultsmentioning

confidence: 99%

Anodic Cyanation of Arylsilanes without Elimination of Silyl Groups

2013

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The electrochemical oxidation of ortho-and meta-anisylsilanes in the presence of sodium cyanide facilitated the direct cyanation of the aromatic ring through the exchange of a hydrogen atom and a cyano group to give cyanoanisylsilanes without elimination of the silyl group. The anodic cyanation of anisylsilanes in methanol and electrophilic reactions of the obtained cyanoanisylsilanes largely depended on the substituted position of the silyl group on the aromatic ring and on the bulkiness of the alkyl group on the silicon atom.

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Section: Resultsmentioning

confidence: 99%