Abstract
The phenylthiyl radical (1) was prepared in the gas phase by vacuum flash pyrolysis of allylphenyl sulfide or diphenyl sulfide and isolated in an argon matrix. The hitherto unknown phenylthiyl peroxy radical was synthesized by co-condensation of 1 with molecular oxygen. Irradiation with light of λ = 465 nm led to a rearrangement to the novel phenylsulfonyl radical.
Highlights
The phenylthiyl radical (1) was prepared in the gas phase by vacuum flash pyrolysis of allylphenyl sulfide or diphenyl sulfide and isolated in an argon matrix
The hitherto unknown phenylthiyl peroxy radical was synthesized by co-condensation of 1 with molecular oxygen
The most useful synthetic applications of the phenylthiyl radical draw on its ability to readily add to carbon–carbon multiple bonds;[9,10,11,12] such additions have been intensively studied by Ito and co-workers.[7,13,14,15,16,17,18,19]
Summary
Generation and characterization of the phenylthiyl radical and its oxidation to the. Cite this: Phys. The observed splitting of the vibrational bands is likely due to the different trapping sites in the argon matrix, which is a common phenomenon.[44] With the aid of the computations, the additional other intense IR bands of medium intensity at 1553, 1433, 1066, 1019, 989, and 415 cmÀ1 are assigned to 1 (Fig. 1, Fig. S1, Table 1 and Table S1, ESI†) Another set of absorption bands located at 1477, 1389, 984, and 801 cmÀ1 provides evidence for the presence of the allyl radical formed as a co-product of the thermal decomposition of 2 (Fig. 1c).
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