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• W2325140024 endingPage "1946" @default.
• W2325140024 startingPage "1938" @default.
• W2325140024 abstract "Rate constants have been calculated, and compared with experimental results, for the cyclizations of 1-carbomethoxy-1-methyl-5-hexenyl radicals (2) with various substituents on C6. The calculations have been done by DFT at the B3LYP/6-311++G** level of theory. They show considerable interaction between C5 and the radical centers even in the ground state of all of the radicals 2. Experimentally, the radicals have been generated by H• transfer to the corresponding acrylate esters 1 and the yields of cyclized products compared to the calculated rate constants. (The “cyclized products” include those from cyclohydrogenation, 4, and those from cycloisomerization, 9.) Two phenyl substituents on C6 (2i), or a phenyl and a methyl substituent (2g, 2h), increase the rate of cyclization, but a single phenyl substituent on C6 produces a greater increase. The calculations show that the two phenyl substituents are twisted in the transition state for cyclization, while a single phenyl substituent remains flat in that transition state. A methyl substituent on C6 along with a single phenyl causes the phenyl to twist in the transition state and decreases the rate constant for cyclization below that of the H/Ph-substituted 2e, 2f." @default.
• W2325140024 created "2016-06-24" @default.
• W2325140024 creator A5022851627 @default.
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• W2325140024 creator A5067684434 @default.
• W2325140024 creator A5072041284 @default.
• W2325140024 date "2014-02-18" @default.
• W2325140024 modified "2023-09-27" @default.
• W2325140024 title "Effect of Double-Bond Substituents on the Rate of Cyclization of α-Carbomethoxyhex-5-enyl Radicals" @default.
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• W2325140024 doi "https://doi.org/10.1021/jo402499w" @default.
• W2325140024 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24502650" @default.
• W2325140024 hasPublicationYear "2014" @default.
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