FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2036854520> ?p ?o ?g. }

• W2036854520 endingPage "6049" @default.
• W2036854520 startingPage "6037" @default.
• W2036854520 abstract "Reaction of a variety of CCH bond-containing 1,6-enynes with N2CHSiMe3 in the presence of RuCl(COD)Cp* as catalyst precursor leads, at room temperature, to the general formation of alkenylbicyclo[3.1.0]hexanes with high Z-stereoselectivity of the alkenyl group and cis arrangement of the alkenyl group and an initial double-bond substituent, for an E-configuration of this double bond. The stereochemistry is established by determining the X-ray structures of three bicyclic products. The same reaction with 1,6-enynes bearing an R substituent on the C1 carbon of the triple bond results in either cyclopropanation of the double bond with bulky R groups (SiMe3, Ph) or formation of alkylidene-alkenyl five-membered heterocycles, resulting from a beta elimination process, with less bulky R groups (R = Me, CH2CH=CH2). The reaction can be applied to in situ desilylation in methanol and direct formation of vinylbicyclo[3.1.0]hexanes and to the formation of some alkenylbicyclo[4.1.0]heptanes from 1,7-enynes. The catalytic formation of alkenylbicyclo[3.1.0]hexanes also takes place with enynes and N2CHCO2Et or N2CHPh. The reaction can be understood to proceed by an initial [2+2] addition of the Ru=CHSiMe3 bond with the enyne CCH bond, successively leading to an alkenylruthenium-carbene and a key alkenyl bicyclic ruthenacyclobutane, which promotes the cyclopropanation, rather than metathesis, into bicyclo[3.1.0]hexanes. Density functional theory calculations performed starting from the model system Ru(HCCH)(CH2=CH2)Cl(C5H5) show that the transformation into a ruthenacyclobutane intermediate occurs with a temporary eta3-coordination of the cyclopentadienyl ligand. This step is followed by coordination of the alkenyl group, which leads to a mixed alkyl-allyl ligand. Because of the non-equivalence of the terminal allylic carbon atoms, their coupling favors cyclopropanation rather than the expected metathesis process. A direct comparison of the energy profiles with respect to those involving the Grubbs catalyst is presented, showing that cyclopropanation is favored with respect to enyne metathesis." @default.
• W2036854520 created "2016-06-24" @default.
• W2036854520 creator A5001422074 @default.
• W2036854520 creator A5015396994 @default.
• W2036854520 creator A5022752792 @default.
• W2036854520 creator A5027305217 @default.
• W2036854520 creator A5048552245 @default.
• W2036854520 creator A5058577382 @default.
• W2036854520 creator A5061370025 @default.
• W2036854520 creator A5077367647 @default.
• W2036854520 creator A5081380476 @default.
• W2036854520 date "2007-04-13" @default.
• W2036854520 modified "2023-10-06" @default.
• W2036854520 title "Selective Ruthenium-Catalyzed Transformations of Enynes with Diazoalkanes into Alkenylbicyclo[3.1.0]hexanes" @default.
• W2036854520 cites W1974525538 @default.
• W2036854520 cites W2003774307 @default.
• W2036854520 cites W2005345467 @default.
• W2036854520 cites W2009253289 @default.
• W2036854520 cites W2016550298 @default.
• W2036854520 cites W2018423656 @default.
• W2036854520 cites W2018928777 @default.
• W2036854520 cites W2020939724 @default.
• W2036854520 cites W2021130826 @default.
• W2036854520 cites W2023271753 @default.
• W2036854520 cites W2023714554 @default.
• W2036854520 cites W2028323841 @default.
• W2036854520 cites W2028476830 @default.
• W2036854520 cites W2028808912 @default.
• W2036854520 cites W2034743818 @default.
• W2036854520 cites W2036780673 @default.
• W2036854520 cites W2038353668 @default.
• W2036854520 cites W2042135581 @default.
• W2036854520 cites W2042611048 @default.
• W2036854520 cites W2045908592 @default.
• W2036854520 cites W2050774198 @default.
• W2036854520 cites W2057665542 @default.
• W2036854520 cites W2074956658 @default.
• W2036854520 cites W2076072148 @default.
• W2036854520 cites W2076522161 @default.
• W2036854520 cites W2078267101 @default.
• W2036854520 cites W2079458939 @default.
• W2036854520 cites W2080629537 @default.
• W2036854520 cites W2082367961 @default.
• W2036854520 cites W2083092622 @default.
• W2036854520 cites W2084049297 @default.
• W2036854520 cites W2088002403 @default.
• W2036854520 cites W2094642658 @default.
• W2036854520 cites W2104022695 @default.
• W2036854520 cites W2107743975 @default.
• W2036854520 cites W2112468447 @default.
• W2036854520 cites W2115652474 @default.
• W2036854520 cites W2129083102 @default.
• W2036854520 cites W2129177368 @default.
• W2036854520 cites W2131433673 @default.
• W2036854520 cites W2143981217 @default.
• W2036854520 cites W2146842987 @default.
• W2036854520 cites W2149642513 @default.
• W2036854520 cites W2155025442 @default.
• W2036854520 cites W2156779917 @default.
• W2036854520 cites W2159072415 @default.
• W2036854520 cites W2167018421 @default.
• W2036854520 cites W2319900189 @default.
• W2036854520 cites W2950794701 @default.
• W2036854520 cites W2951136978 @default.
• W2036854520 cites W2951333144 @default.
• W2036854520 cites W2952094157 @default.
• W2036854520 cites W2952220235 @default.
• W2036854520 cites W2952330213 @default.
• W2036854520 cites W2952842814 @default.
• W2036854520 cites W2952920377 @default.
• W2036854520 doi "https://doi.org/10.1021/ja0700146" @default.
• W2036854520 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/17429974" @default.
• W2036854520 hasPublicationYear "2007" @default.
• W2036854520 type Work @default.
• W2036854520 sameAs 2036854520 @default.
• W2036854520 citedByCount "105" @default.
• W2036854520 countsByYear W20368545202012 @default.
• W2036854520 countsByYear W20368545202013 @default.
• W2036854520 countsByYear W20368545202014 @default.
• W2036854520 countsByYear W20368545202015 @default.
• W2036854520 countsByYear W20368545202016 @default.
• W2036854520 countsByYear W20368545202017 @default.
• W2036854520 countsByYear W20368545202018 @default.
• W2036854520 countsByYear W20368545202019 @default.
• W2036854520 countsByYear W20368545202020 @default.
• W2036854520 countsByYear W20368545202021 @default.
• W2036854520 countsByYear W20368545202022 @default.
• W2036854520 countsByYear W20368545202023 @default.
• W2036854520 crossrefType "journal-article" @default.
• W2036854520 hasAuthorship W2036854520A5001422074 @default.
• W2036854520 hasAuthorship W2036854520A5015396994 @default.
• W2036854520 hasAuthorship W2036854520A5022752792 @default.
• W2036854520 hasAuthorship W2036854520A5027305217 @default.
• W2036854520 hasAuthorship W2036854520A5048552245 @default.
• W2036854520 hasAuthorship W2036854520A5058577382 @default.
• W2036854520 hasAuthorship W2036854520A5061370025 @default.
• W2036854520 hasAuthorship W2036854520A5077367647 @default.
• W2036854520 hasAuthorship W2036854520A5081380476 @default.

• next