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Tricyclic Heterocycles with Bifunctional Silicon Centers by Joyce C. Corey; Christy S. John; Martha C. Ohmsted; Lihsueh S. Chang is a Chemistry article available to read on EtoBox.

What is Tricyclic Heterocycles with Bifunctional Silicon Centers about?

Condensation of the diorganometallic reagents, (o-MC,H,),X (M = Li, MgCl) with HSiCl, followed by reduction with LiAlH, provides dibenzosilacycles, I (a, X = -; b, X = NMe; c, X = CH,; d, X = CH,CH2) with two exocyclic H-substituents , >SiH,. Conditions for the stepwise conversion of I to mixed bifunctional systems, >SiHX (II, X = Cl, Br; III, X = OR), and bifunction~ derivatives, >SiX, (IV, X = Cl; V, X = OR) were determined. Controlled halogenation of I to II was accomplished with one molar equivalent of SO&l, or NBS although Ccl, in the presence of ClRh(PPh,), or PdCl, results in slow monochlorination. The reaction of I with excess SOCI, or SO&l, converts I to III but the latter is faster and provides fewer side reactions. Conversion of I to IV with excess alcohols occurs in high yield with ClRh(PPh,), but in low yield with H,PtCl,. Controlled alcoholysis of I to III could not be achieved except with 'BuOH. The dichlorides, IV, are methylated in high yield to VII, , 'SiM%. Reaction of Ib with ClRh(PPh,), results in elimination of H, and formation of disilanes as indicated by trapping reactions with alcohols (formation of Vb). 0022-328X/86/$03.50 0 1986 Elsevier Sequoia S.A. ' Ex

Who reads Tricyclic Heterocycles with Bifunctional Silicon Centers?

Author

Joyce C. Corey; Christy S. John; Martha C. Ohmsted; Lihsueh S. Chang

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-328X)

Published

1986

Language

EN

Field

Chemistry (Physical Sciences)