A new synthesis of 2-fluoro-1-olefins

First Detection of a Selenenyl Fluoride ArSeF by NMR Spectroscopy: The Nature of Ar2Se2/XeF2 and ArSeSiMe3/XeF2 Reagents

“…PhSeF equivalents are also generated from PhSeEMe 3 (E = Si, Ge, Sn, Pb) and XeF 2 13 or from PhSeOTf/Et 3 N⋅3 HF 14. Also the combinations PhSeBr/AgF/ultrasound,15 PhSeCl/AgF/CH 3 CN,16 N ‐phenylselenophthalimide (NPSP)/Py⋅9 HF,17 or NPSP/Et 3 N⋅3 HF18 and electro oxidation of Ph 2 Se 2 in Et 3 N⋅3 HF19 act as PhSeF equivalents. None of these procedures offer more detailed information about the nature of the reacting species.…”

Use of phenylselenyl chloride in the preparation of methyl 11‐phenylseleno‐10‐acetamido‐ and ethyl phenylselenoethoxy fatty alkanoates

“…The abbreviations s, m, t, q, and br stand for singlet, multiplet, triplet, quartet, and broad, respectively. Major diagnostic fragments in MS are shown in Figures 2,4,and 5. TLC plates (20 × 5 cm) were prepared in the laboratory and were coated with a layer of silica gel G (0.25 mm thickness; Merck, Mumbai, India) and a mixture of petroleum ether/ diethyl ether/acetic acid (80:20:1, by vol) was normally used as the developing solvent. Compounds on the TLC plates were visualized by charring the sprayed plates with a 20% aqueous solution of perchloric acid.…”

“…A literature survey revealed that phenylselenyl reagents participate in a number of useful reactions such as addition (1)(2)(3)(4), cyclization (5)(6)(7), and others (8)(9)(10). These phenylselenyl reagents also are used in a number of reactions involving unsaturated compounds (11)(12)(13) to form aminoselenides and alkanones and for the effective introduction of unsaturated functionality (14,15).…”

Synthetic approaches to monofluoroalkenes

“…In 1990, McCarthy and coworkers reported the first trans-addition of phenylselenenyl fluoride to C-C double bonds to provide b-fluoro phenylselenides which could be converted, when terminal alkenes were used, into a-fluorovinyl compounds (Scheme 3). 22 The selenium species is formed in situ by the reaction of phenylselenenyl chloride with AgF in acetonitrile. The yields for the addition of PhSeF widely vary from poor to excellent (31-94%) whereas those for the oxidation/ elimination are good to excellent (66-83%).…”