ja7b10325_si_002.cif (3.77 MB)
Facile Conversion of Bis-Silylene to Cyclic Silylene Isomers: Unexpected C–N and C–H Bond Cleavage
dataset
posted on 2017-11-01, 00:00 authored by Yuzhong Wang, Hunter P. Hickox, Yaoming Xie, Pingrong Wei, Henry F. Schaefer, Gregory H. RobinsonReaction
of thiolate 1 with carbene-stabilized diiodo-bis-silylene
(2) (in a 2:1 ratio) in THF unexpectedly gives both the
first five-membered, sulfur-containing, zwitterionic silylene ring
(3) via insertion of the “SiI2” unit of 2 into the olefinic CH bond
of the imidazole ring of 1 and four-membered cyclic silylene
(4) via insertion of a silicon(I) atom of 2 into the CphenylN bond of the carbene ligand.
The parallel reaction in toluene only gives 3 as the
major product. The nature of the bonding in isomeric 3 and 4 was probed by experimental and theoretical methods.
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isomeric 3Cyclic Silylene Isomerscarbene ligandfive-memberedFacile Conversionfour-membered cyclic silyleneinsertionTHFcarbene-stabilized diiodo-bis-silyleneratiophenylmethodBis-Silyleneimidazole ringtolueneolefinicsulfur-containingUnexpectedCleavageBondzwitterionic silylene ringsiliconbondnaturethiolate 1
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