Synthesis of Arenesulfenyl Fluorides and Fluorosulfenylation of Alkenes, Alkynes, and α-Diazocarbonyl Compounds.

Sulfenyl fluorides are organic compounds of sulfur in formal oxidation state +2 with the formula R-S-F. Although the chloride, bromide, and iodide analogues have been extensively described in the literature, arenesulfenyl fluorides remain essentially unstudied. These structures have been implicated as putative intermediates in established processes to access polyfluorinated sulfur species; however, definitive and direct evidence of their existence has not been obtained, nor has a systematic understanding of their reactivity.

A synthesis of novel expanded porphyrinoids: Ni-induced nitrile cyclization of dicyanovinylene-bis(meso-aryl)dipyrrin.

Ni-Metallation of dicyanovinylene-bis(meso-aryl)dipyrrin 1 under refluxed toulene conditions resulted in the formation of a bicyclic pyrrolizine ring to afford two isomeric bisNi expanded porphyrinoid complexes 2a and 2b. Furthermore, acyclic Ni dipyrrin complex 3 was also isolated. The respective structures for 2a, 2b, and 3 were elucidated by X-ray diffraction analysis.