Aminoethynyl-silanes, -germanes and -stannanes: novel organometallic-substituted enamines via 1,1-organoboration
✍ Scribed by Bernd Wrackmeyer; Oleg L. Tok; Gudrun Guldner; Sergej V. Gruener
- Publisher
- John Wiley and Sons
- Year
- 2003
- Tongue
- English
- Weight
- 168 KB
- Volume
- 17
- Category
- Article
- ISSN
- 0268-2605
- DOI
- 10.1002/aoc.533
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✦ Synopsis
Abstract
The reactions of diethylaminoethynyl(trimethyl)silane (1), bis(diethylaminoethynyl)methylsilane (2), diethylaminoethynyl(trimethyl)germane (3), dimethylaminoethynyl(triethyl)germane (4), diethylaminoethynyl(trimethyl)stannane (5) and methyl(phenyl)aminoethynyl(trimethyl)stannane (6) with trialkylboranes [BEt~3~ (7b), BPr~3~ (7c), B^i^Pr~3~ (7d) and 9‐alkyl‐9‐borabicyclo[3.3.1]nonanes 9‐Me‐9‐BBN (8a) and 9‐Et‐9‐BBN (8b)] were studied. The alkynes 1 and 2 did not react even with boiling BEt~3~, whereas the reactions of 3–6 afforded mainly novel enamines [(E)‐1‐amino‐1‐trialkylgermyl‐2‐dialkylboryl‐alkenes (9, 10), (E)‐1‐diethylamino‐1‐trimethylstannyl‐2‐dialkylboryl‐alkenes (11, 12), (E)‐1‐methyl(phenyl)amino‐1‐trimethylstannyl‐2‐dialkylboryl‐alkenes (13, 14)]. This particular stereochemistry is unusual for products from 1,1‐organoboration reactions, indicating a special influence of the amino group. The starting materials and products were characterized by multinuclear magnetic resonance spectroscopy (^1^H, ^11^B, ^13^C, ^15^N, ^29^Si, ^119^Sn NMR). Copyright © 2003 John Wiley & Sons, Ltd.