Matches in SemOpenAlex for { <https://semopenalex.org/work/W2059777002> ?p ?o ?g. }
- W2059777002 endingPage "3370" @default.
- W2059777002 startingPage "3357" @default.
- W2059777002 abstract "The anionic [3 + 2] cycloaddition of allyl anions or allyllithium compounds to double or triple bonds is an elegant route both to carbocyclic and to heterocyclic five-membered rings. The mechanism of such reactions has not yet been established conclusively. In this computational study, the concerted 4πs + 2πs mechanism, expected on the basis of the Woodward−Hoffmann rules, is found to be less favorable than two-step pathways for the cycloadditions of ethylene to the allyl, 2-borylallyl, and 2-azaallyl anions and their lithiated counterparts at Becke3LYP/6-311+G** and MP2(fc)/6-31+G* levels of theory. Except for allyllithium, the 4πs + 2πs cycloadditions (in Cs symmetry) are not concerted, since only second-order saddle points, rather than true transition structures, are involved. The anisotropy of the reactant polarizabilities is responsible. Instead, two-step cycloaddition pathways are followed by all three model systems. In accord with experimental experience, 2-borylallyl and 2-azaallyl compounds are found to undergo this type of reaction more readily than the unsubstituted allyl anion or allyllithium. The second, ring-closing step is facilitated by the anion-stabilizing effect of nitrogen and the boryl substituent." @default.
- W2059777002 created "2016-06-24" @default.
- W2059777002 creator A5011835456 @default.
- W2059777002 creator A5061189766 @default.
- W2059777002 creator A5082053493 @default.
- W2059777002 date "1998-03-31" @default.
- W2059777002 modified "2023-10-17" @default.
- W2059777002 title "Mechanism of Anionic [3 + 2] Cycloadditions. An ab Initio Computational Study on the Cycloaddition of Allyl-, 2-Borylallyl-, and 2-Azaallyllithium to Ethylene" @default.
- W2059777002 cites W141967380 @default.
- W2059777002 cites W1516933842 @default.
- W2059777002 cites W1963685029 @default.
- W2059777002 cites W1964550277 @default.
- W2059777002 cites W1965752906 @default.
- W2059777002 cites W1967865588 @default.
- W2059777002 cites W1967981248 @default.
- W2059777002 cites W1968314378 @default.
- W2059777002 cites W1968545176 @default.
- W2059777002 cites W1971174708 @default.
- W2059777002 cites W1971275758 @default.
- W2059777002 cites W1972952197 @default.
- W2059777002 cites W1974682021 @default.
- W2059777002 cites W1978726598 @default.
- W2059777002 cites W1979462524 @default.
- W2059777002 cites W1980949882 @default.
- W2059777002 cites W1981046912 @default.
- W2059777002 cites W1983038499 @default.
- W2059777002 cites W1983318841 @default.
- W2059777002 cites W1985118314 @default.
- W2059777002 cites W1987302970 @default.
- W2059777002 cites W1989095487 @default.
- W2059777002 cites W1995939432 @default.
- W2059777002 cites W1996408277 @default.
- W2059777002 cites W2000240980 @default.
- W2059777002 cites W2000481470 @default.
- W2059777002 cites W2008514914 @default.
- W2059777002 cites W2008526825 @default.
- W2059777002 cites W2014500973 @default.
- W2059777002 cites W2018687079 @default.
- W2059777002 cites W2018920919 @default.
- W2059777002 cites W2019606902 @default.
- W2059777002 cites W2024649752 @default.
- W2059777002 cites W202638607 @default.
- W2059777002 cites W2029848743 @default.
- W2059777002 cites W2040342773 @default.
- W2059777002 cites W2040899835 @default.
- W2059777002 cites W2046469777 @default.
- W2059777002 cites W2050074098 @default.
- W2059777002 cites W2050815971 @default.
- W2059777002 cites W2051300466 @default.
- W2059777002 cites W2058197373 @default.
- W2059777002 cites W2058293865 @default.
- W2059777002 cites W2060372290 @default.
- W2059777002 cites W2067528435 @default.
- W2059777002 cites W2069480716 @default.
- W2059777002 cites W2070430253 @default.
- W2059777002 cites W2072897451 @default.
- W2059777002 cites W2073556826 @default.
- W2059777002 cites W2074661241 @default.
- W2059777002 cites W2074830856 @default.
- W2059777002 cites W2087123115 @default.
- W2059777002 cites W2091005641 @default.
- W2059777002 cites W2091687583 @default.
- W2059777002 cites W2094159250 @default.
- W2059777002 cites W2094657594 @default.
- W2059777002 cites W2105474414 @default.
- W2059777002 cites W2119150442 @default.
- W2059777002 cites W2120507039 @default.
- W2059777002 cites W2130005898 @default.
- W2059777002 cites W2136616050 @default.
- W2059777002 cites W2139046232 @default.
- W2059777002 cites W2139843296 @default.
- W2059777002 cites W2143981217 @default.
- W2059777002 cites W2148284063 @default.
- W2059777002 cites W2153223962 @default.
- W2059777002 cites W2170629647 @default.
- W2059777002 cites W2171061620 @default.
- W2059777002 cites W2171821261 @default.
- W2059777002 cites W2172180843 @default.
- W2059777002 cites W2318908709 @default.
- W2059777002 cites W2835922784 @default.
- W2059777002 cites W2949144143 @default.
- W2059777002 cites W2950041316 @default.
- W2059777002 cites W2951869189 @default.
- W2059777002 cites W3004670478 @default.
- W2059777002 cites W4243187414 @default.
- W2059777002 cites W4246536672 @default.
- W2059777002 cites W4252966993 @default.
- W2059777002 cites W74761523 @default.
- W2059777002 cites W1976609767 @default.
- W2059777002 cites W1994822965 @default.
- W2059777002 cites W2126878840 @default.
- W2059777002 doi "https://doi.org/10.1021/ja9735160" @default.
- W2059777002 hasPublicationYear "1998" @default.
- W2059777002 type Work @default.
- W2059777002 sameAs 2059777002 @default.
- W2059777002 citedByCount "34" @default.
- W2059777002 countsByYear W20597770022014 @default.
- W2059777002 countsByYear W20597770022015 @default.