Reactions of Alkenes and Alkynes with an Acyclic Silylene and Heavier Tetrylenes under Ambient Conditions
Lips, F., Mansikkamäki, A., Fettinger, J. C., Tuononen, H., & Power, P. P. (2014). Reactions of Alkenes and Alkynes with an Acyclic Silylene and Heavier Tetrylenes under Ambient Conditions. Organometallics, 33(21), 6253-6258. https://doi.org/10.1021/om500947x
© 2014 American Chemical Society. This is a final draft version of an article whose final and definitive form has been published by ACS. Published in this repository with the kind permission of the publisher.
Cycloaddition reactions of the acyclic silylene Si(SAriPr4)2 (AriPr4 = C6H3-2,6(C6H3-2,6-iPr2)2) with a variety of alkenes and alkynes were investigated. Its reactions with the alkynes phenylacetylene and diphenylacetylene and the diene 2,3-dimethyl-1,3-butadiene yielded silacycles (AriPr4S)2tiebar above startSi(CH═tiebar above endCPh) (1), (AriPr4S)2tiebar above startSi(PhC═tiebar above endCPh) (2), and (AriPr4S)2tiebar above startSiCH2CMeCMetiebar above endCH2 (3) at ambient temperature. The compounds were characterized by X-ray crystallography, 1H, 13C, and 29Si NMR spectroscopy, and IR spectroscopy. No reaction was observed with more substituted alkenes such as propene, (Z)-2-butene, tert-butylethylene, cyclopentene, 1-hexene, or the alkyne bis(trimethylsilyl)acetylene under the same reaction conditions. The germylene Ge(SArMe6)2 and stannylene Sn(SArMe6)2 (ArMe6 = C6H3-2,6(C6H2-2,4,6-Me3)2) analogues of Si(SArMe6)2 displayed no reaction with ethylene. Quantum chemical calculations using model tetrylenes E(SPh)2 (E = Si, Ge, Sn; Ph = C6H5) show that cyclization reactions are endothermic in the case of germanium and tin derivatives but energetically favored for the silicon species. ...
PublisherAmerican Chemical Society
Publication in research information system
MetadataShow full item record
Showing items with similar title or keywords.
Lips, Felicitas; Fettinger, James C.; Mansikkamäki, Akseli; Tuononen, Heikki; Power, Philip (American Chemical Society, 2014)Treatment of toluene solutions of the silylenes Si(SArMe6)2 (ArMe6 = C6H3-2,6(C6H2-2,4,6-Me3)2, 1) or Si(SArPri4)2 (ArPri4 = C6H3-2,6(C6H3-2,6-Pri2)2, 2) with excess ethylene gas affords the siliranes (ArMe6S)2tiebar above ...
Saarinen, Kati; Laakso, Jouni; Lindström, Leena; Ketola, Tarmo (Blackwell Publishing Ltd, 2018)Rapid environmental fluctuations are ubiquitous in the wild, yet majority of experimental studies mostly consider effects of slow fluctuations on organism. To test the evolutionary consequences of fast fluctuations, we ...
Ambient Play : Larissa Hjorth & Ingrid Richardson. Ambient Play. Cambridge, Massachusetts: The MIT Press, 2020. Järvenpää, Hanna (Pelitutkimuksen seura, 2021)
Liikunnan toimintapolitiikan arviointia terveyden edistämisen kontekstissa : sosiaalisen tuen, fyysisen ympäristön ja poliittisen ympäristön yhteys liikunta-aktiivisuuteen Ståhl, Timo (Jyväskylän yliopisto, 2003)The purpose of this study was to examine the relationships between reported physical activity and physical environment, policy environment and social support. The aim was to evaluate the success of the policy for physical ...
Tiihonen, Jari; Halonen, Pirjo; Tiihonen, Laura; Kautiainen, Hannu; Storvik, Markus; Callaway, James (Nature Publishing Group, 2017)It is controversial if global warming will result into increased crime and conflict rate, and no causal neurobiological mechanisms have been proposed for the putative association between ambient temperature and aggressive ...