Intramolecularly donor-stabilized silenes: Part 5. Generation and conversion of 1-[2,6-bis(alkoxymethyl)phenyl]- and 1-(8-alkoxynaphthyl)-1,2,2-tris(trimethylsilyl)silenes

1-(8-Methoxy-1-naphthyl)-1,2,2-tris(trimethylsilyl)silene (10) and the 1-[2,6-bis(alkoxymethyl)phenyl]-1,2,2-tris(trimethylsilyl)silenes (12a–d) were generated by the reaction of (dichloromethyl)tris(trimethylsilyl)silane (1) with two molar equivalents of 8-methoxy-1-naphthyllithium or 2,6-bis(alkoxymethyl)phenyllithium (8a–d), respectively, but proved to be unstable. 10 was trapped with excess of the applied naphthyllithium reagent to give 1,1-bis(8-methoxy-1-naphthyl)-1-[bis(trimethylsilyl)methyl]-2,2,2-trimethyldisilane (11); and 12a–d underwent spontaneous conversions and formed two types of substituted 2-oxa-1-silaindane derivatives (13a,b and 14b–d). Whereas silenes with an intramolecular amine coordination are thermally stable compounds which can be isolated, the intramolecular coordination of an ether group to the electrophilic silene silicon atom does not provide a comparable stabilization to the SiC system and the respective derivatives generated were converted into resultant products.