2006
DOI: 10.1016/j.jfluchem.2006.03.006
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Experimental and theoretical studies on the transannular cyclizations of 3,7-dimethylenebicyclo[3.3.1]nonane with polyfluoroalkyl radicals

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Cited by 18 publications
(10 citation statements)
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“…Such a set of products unequivocally evidences for the electrophilic addition mechanism as differently substituted double bonds are not discriminated. Such selectivities are in sharp contrast with those observed for the reactions of 1 a and 1 b with perfluoroalkyl radicals20c or neutral electrophiles20a and are in accord with computed model reaction of 1 a with the F + ⋅⋅⋅ H 2 O complex (Figure 4).…”
Section: Resultssupporting
confidence: 84%
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“…Such a set of products unequivocally evidences for the electrophilic addition mechanism as differently substituted double bonds are not discriminated. Such selectivities are in sharp contrast with those observed for the reactions of 1 a and 1 b with perfluoroalkyl radicals20c or neutral electrophiles20a and are in accord with computed model reaction of 1 a with the F + ⋅⋅⋅ H 2 O complex (Figure 4).…”
Section: Resultssupporting
confidence: 84%
“…Fortunately, compound 1 allows us distinguish between the radical and non‐radical addition modes because the reaction of 1 with radicals gives noradamantane derivatives predominantly,20c, 21b in contrast to the reactions with electrophiles that lead to substituted adamantanes 21a. 23 We found that this is indeed true for treatment of 1 with the F radical (Figure 3).…”
Section: Resultsmentioning
confidence: 77%
“…Using the DFT method, we have established that formation of noradamantane derivatives at cyclization of diene 1 with electrophilic trifluoromethyl radical corresponds to kinetic control [31]. This allowed us to assign of noradamantane product 2 forming through the radical mechanism.…”
Section: Transannular Cyclization 37-dimethylenebicyclo[331]nonanementioning
confidence: 96%
“…It has been previously shown, that transannular cyclization of bicyclo[3.3.1]nonane dienes with radical agents (CCl 4 /AIBN [29], C 6 H 5 SH, CH 3 PhSO 2 Hlg (Hlg = Cl, Br) [30]) and with polyfluoroalkyl radicals [31] gives mainly noradamantane derivatives. Using the DFT method, we have established that formation of noradamantane derivatives at cyclization of diene 1 with electrophilic trifluoromethyl radical corresponds to kinetic control [31].…”
Section: Transannular Cyclization 37-dimethylenebicyclo[331]nonanementioning
confidence: 99%
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