279-35-6Relevant articles and documents
Adam,Eggelte
, (1977)
Triphenylphosphine reduction of saturated endoperoxides
Erden, Ihsan,Gaertner, Christian,Saeed Azimi
supporting information; experimental part, p. 3986 - 3989 (2009/12/05)
(Figure Presented) Triphenylphosphine reduction of saturated endoperoxides derived from 6,6-dimethylfulvene and spiro[2.4]hepta-4,6-diene in the presence of nucleophiles results in the formation of products that mainly stem from deoxygenation followed by carbocation formation. Nucleophilic attack by solvent proceeds by an SN1 like mechanism; allyl shifts and cyclopropylcarbinyl-cyclobutyl rearrangements also occur. With the systems lacking carbocation-stabilizing groups, the deoxygenation step is preceded by attack of H2O at the phosphorus.
Time-resolved infrared studies of triplet 1,3-cyclopentanediyl
Showalter, Brett M.,Bentz, Timothy C.,Ryzhkov, Lev R.,Hadad, Christopher M.,Toscano, John P.
, p. 309 - 312 (2007/10/03)
Triplet-sensitized photolysis of 2,3-diazabicyclo[2.2.1]hept-2-ene (1) in argon- or oxygen- saturated acetonitrile-d3 solutions results in the formation of bicyclo[2.1.0]pentane (3), a ring closure product arising from an intermediate 1,3-cyclopentanediyl triplet biradical (2). Time-resolved infrared (TRIR) spectroscopy was used to monitor the kinetics of bicyclopentane 3 production. This analysis provides a measurement of the triplet biradical lifetime and an estimate of the bimolecular reaction rate between biradical 2 and oxygen, both in good agreement with previous investigations. Our studies also indicate that certain IR bands due to 3 in the C-H stretching region overlap with corresponding bands in biradical 2. This interpretation is supported by computational investigations. Copyright
CONVERSION OF BICYCLOPENTANE INTO 2,3-DIOXABICYCLOHEPTANE VIA t-BUTYL PEROXYMERCURIATION
Bloodworth, A. J.,Hargreaves, Neville
, p. 2783 - 2784 (2007/10/02)
Bicyclopentane has been converted in 45 percent yield into 2,3-dioxabicycloheptane by the sequence t-butyl peroxymercuriation, iodomercuriation, epimerisation of the resultant 1-t-butylperoxy-3-iodocyclopentane, and reaction of the trans isomer with silver trifluoroacetate.