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Insertion of Metal-substituted Silylene into Naphthalene's Aromatic Ring and Subsequent Rearrangement for Silaspiro-benzocycloheptenyl and Cyclobutenosilaindan Derivatives.

Synthesis of silacycle compounds are of fundamental and application importance. Herein we report the first example of insertion of metal-substituted silylene fragment into naphthalene's aromatic ring. More significantly, this insertion is followed by interesting rearrangements to yield silaspiro-benzocycloheptenyl and cyclobutenosilaindan derivatives. The formation of cyclobutenosilaindan derivative includes the C-C bond cleavage and 4π electrocyclization steps; the formation of silaspiro-benzo-cycloheptenyl derivative is more complicated, including the C-C bond cleavage, reversible 4π electrocyclization, C-H bond activation and C-Si bond cleavage. DFT investigations were carried out to shed light on the mechanistic aspects of these two rearrangements. The formed cyclobutenosilaindan potassium can readily react with PhOH, MeOTf, EtOTf, PhCH 2 Cl or PhCOCl at room temperature to afford the hydrogen, alkyl, benzyl or benzoyl substituted cyclobutenosilaindans in high yields.