Journal
ORGANOMETALLICS
Volume 37, Issue 15, Pages 2399-2405Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.8b00197
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Funding
- National Natural Science Foundation of China [21472032, 21771048]
- Natural Science Foundation of Zhejiang Province [LY17B010002]
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The reactions of stable monomeric dialkyl-stannylene 1 with methyl and ethyl propynoates give the corresponding 1:2 adducts, alkenyl(alkynyl)stannane 2 and 3 in high yields, while 1 does not react with parent acetylene or common mono- and disubstituted acetylenes such as phenylacetylene, trimethylsilylacetylene, diethyl 2-butynedioate, etc. Notably, 2 and 3 have the Z-configuration of the alkenyl moieties, in contrast to similar adducts obtained by the known reactions of silylenes with terminal acetylenes. It is suggested that the formation of a carbonyl oxygen-coordinate cyclic zwitterion as a key intermediate is essential for the reactions. Stannylene 1 adds to in situ generated benzyne, forming a 1:1 adduct having a unique 3-stanna-1-silaindane ring system.
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