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Exploring the cyclization reaction channel for the gas-phase elementary reaction between the silicon nitride radical (SiN; X2Σ+) and isoprene (C5H8; X1A′) to prepare methylazasilacyclohexadienylidenes (SiNC5H7; X1A′)
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DOI：10.1039/D5CP04314J.png)
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Abstract
En 中文
Silicon-containing heterocyclic molecules have emerged as promising candidates in medicinal and agrochemical research. However; the synthesis of silicon-containing heterocycles has remained highly challenging. In this work; we employed the crossed molecular beams technique to elucidate the underlying reaction pathways for the synthesis of a unique class of six-membered cyclic organosilicon molecules in which silicon and nitrogen atoms occupy adjacent positions: methyl-azasilacyclohexadienylidenes – silicon and nitrogen substituted benzenes functionalized with a methyl group. This class was accessed via the reaction of ground-state silicon nitride radicals (SiN; X2Σ+) with isoprene (C5H8; X1A′) under single-collision conditions at a collision energy of 25 ± 1 kJ mol−1. Integration of experimental results with electronic structure calculations revealed the formation of at least two cyclic products: 4-methyl-1-aza-2-silacyclohexa-3; 5-dien-2-ylidene and 5-methyl-1-aza-2-silacyclohexa-3; 5-dien-2-ylidene. The underlying mechanism shows strong similarities to the previously studied reaction of the silicon nitride radicals (SiN; X2Σ+) with 1; 3-butadiene (C4H6; X1Ag); with the methyl group in isoprene classified as a spectator; thus advancing our fundamental understanding of the organosilicon chemistry through the delivery of synthetic pathways to a distinct class of silicon-containing heterocyclic molecules: methylazasilacyclo-hexadienylidenes.
Keywords:
silicon-containing heterocycles
silicon nitride radicals
isoprene
cyclization reaction
organosilicon chemistry
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