ISSN:
0009-2940
Keywords:
Silanes, alkynyl[(trimethylstannyl)ethynyl]-
;
1,1-Ethyloboration, intermolecular
;
1,1-Vinyloboration, intramolecular
;
Siloles
;
Protodeborylation
;
Protodestannylation
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of alkynyl[(trimethylstannyl)ethynyl]dimethylsilanes 4 [alkynyl R1 - C≡C: R1 = Bu (b), tBu (c), iPent (d), Ph (e), SiMe3 (f)] is reported. The intermolecular 1,1-ethyloboration of 4 with triethylborane takes place selectively at the Sn - C≡ bond to give first the alkenyl(alkynyl)dimethylsilanes 5 and 6. There exists an equilibrium between 5 and 6, and compound 6 has the suitable stereochemistry for the final intramolecular 1,1-vinyloboration to form the 4-(diethylboryl)-2-(trimethylstannyl)siloles 7. Protodeborylation of 7 with water gives the 2-(trimethylstannyl)siloles 8, and protodeborylation and protodestannylation with an excess of acetylacetone affords the siloles 9. Multinuclear NMR (1H-, 11B-, 13C-, 29Si-, and 119Sn-) serves for monitoring the reactions and for the characterization of the products.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931261009
