Add time:07/20/2019 Source:sciencedirect.com
The transient silenes (Me3Si)2SiCR1R2 (4: R1=H, R2=2-Me2N-5-Me–C6H3; 11: R1=Me, R2=2-Me2N–C6H4; 15: R1=3,5-Me2–C6H3, R2=2-Me2N–C6H4; 18: R1=Me, R2=2-Me2N-5-Me–C6H3) were generated following the mechanism of the sila-Peterson reaction. Thus, 4 was obtained by base-induced trimethylsilanol elimination from (2-dimethylamino-5-methylphenyl)tris(trimethylsilyl)silylmethanol (3). Addition of methyllithium or 3,5-dimethylphenyllithium, respectively, to the carbonyl group of 2-dimethylaminobenzoyl-tris(trimethylsilyl)silane (10) and subsequent elimination of Me3SiOLi led to 11 and 15, respectively. Similarly, (2-dimethylamino-5-methylbenzoyl)-tris(trimethylsilyl)silane (17) and MeLi gave 18. The silene 4 underwent a spontaneous head-to-tail cyclodimerization to give a 1,3-disilacyclobutane (5), whereas 11 afforded a linear head-to-head dimer (12). The dimerization rates of 15 and 18 proved to be slow, thus, under the conditions of the sila-Peterson reaction readdition products of eliminated trimethylsilanolate to the SiC bond of the silenes were obtained (16, 19). The structures of the compounds prepared were elucidated on the basis of comprehensive NMR and MS studies; for 5 also the results of an X-ray structural analysis are given. Possible reasons for the different behavior of the similarly structured silenes are discussed.
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