40548-64-9Relevant articles and documents
PHOTOSTIMULATED REACTIONS OF NEOPENTYL IODIDES WITH CARBANIONS IN DMSO BY THE SRN1 MECHANISM
Penenory, Alicia B.,Rossi, Roberto A.
, p. 605 - 610 (2007/10/03)
Neopentyl iodide, 1, reacted under photostimulation with several carbanionic nucleophiles in DMSO.With acetone enolate ion only reduction and dimerization occured, but good yields of substitution products have been obtained with acetophenone, 5, and anthrone, 9, anions as nucleophiles.Nitromethane anion, 7, does not react with 1 under irradiation, but good yields of the substitution products are obtained when the photostimulated reaction is carried out in the presence of acetone enolate ions (entrainment reaction).Inhibition experiments by p-dinitrobenzene and by the radical trap TEMPO, suggest that these reactions occur by the SRN1 mechanism of nucleophilic substitution.The photostimulated reaction of 1,3-diiodo-2,2-dimethylpropane, 15, with 5 gave the disubstitution product 17 and the reduced monosubstitution product 18.It has been found that the monosubstitution product 16 (in which iodine is retained) is not an intermediate of these reactions. 1-iodoadamantane, 12, is more reactive (ca. 4.9 times) than 1 in competitive experiments toward 5 and under photostimulation.