STUDIES IN SILICO-ORGANIC COMPOUNDS. VII. THE PREPARATION AND PROPERTIES OF CERTAIN SUBSTITUTED SILANES¹

A Novel Phenol for Use in Convergent and Divergent Dendrimer Synthesis: Access to Core Functionalisable Trifurcate Carbosilane Dendrimers—The X-ray Crystal Structure of [1,3,5-Tris{4-(triallylsilyl)phenylester}benzene]

“…]. This halosilane was first produced over forty years ago by Scott and Frisch; [12] however, their procedure involves a nonselective reaction of allylmagnesium bromide (3 equiv) with SiCl in diethyl ether, [13] in order to avoid this tedious purification procedure. Compound 3 was then converted to 2 (72 % yield) by treatment with cupric chloride (2 equiv) in boiling acetonitrile in the presence of an organic base, followed by extraction with pentane (see Experimental Section).…”

“…to yield a dark brown, oily solution. Triallylsilane 3 [13] (5.96 g, 39.2 mmol) was added to this mixture at RT and the contents of the reaction flask were subsequently heated to 80 8C overnight. The resulting dark brown suspension was extracted with pentane (3 Â 75 mL) under nitrogen and was filtered, and the pentane extracts were combined.…”

“…Infrared spectra were recorded in solution with a Unicam FT-IR 5000 spectrophotometer. The 1 H (200 and 300 MHz) and 13 C{ 1 H} (50 and 75 MHz) NMR spectra were recorded at RT (298 K) with a Bruker AC 200, WH 200 or AC 300 instrument with SiMe 4 as the external standard with the samples in CDCl 3 solution, unless otherwise stated. Flash chromatography was performed on silica (230 ± 400 mesh, Merck).…”

“…in diethyl ether, [13] in order to avoid this tedious purification procedure. Compound 3 was then converted to 2 (72 % yield) by treatment with cupric chloride (2 equiv) in boiling acetonitrile in the presence of an organic base, followed by extraction with pentane (see Experimental Section).…”

“…Displacement ellipsoid (50 % probability) plot of 7 (hydrogen atoms are omitted for clarity). Selected bond lengths []: Si1ÀC18 1.857(7), Si1ÀC111 1.848(6), Si1ÀC114 1.883(8), Si2ÀC28 1.877(6), Si2ÀC211 1.900(6), Si2ÀC214 1.879(6), Si3ÀC38 1.875(5), Si3ÀC311 1.866(6), Si3ÀC314 1.891(6), C18ÀC19 1.450(14), C111ÀC112 1.496(7), C114ÀC115 1.483 (13), C28ÀC29 1.489(8), C211ÀC212 1.494(11), C214ÀC215 1.457(7), C38ÀC39 1.485(8), C311ÀC312 1.495(10), C314ÀC315 1.482(10), C19ÀC110 1.217(14), C112ÀC213 1.340(11), C215ÀC316 1.292 (10). Interplanar angles [8] between the least-squares planes of the central benzene ring and of C12ÀC17: 87.62 (18), of C22ÀC27: 74.53(19) and of C32ÀC37: 78.80 (19).…”