From oxides of internal perfluoroolefins to fluorocontaining camphor thiazolinylhydrazones

When two symmetrically independent molecules must be different: “Crystallization-induced diastereomerization” of chiral pinanyl sulfone

“…1 The significantly fewer amount of Z′ = 2 structures, which are presented in the literature, are characterized by distinctions in kind between molecules A and B, which can consist of either conformation or (which is more uncommon) configuration of one or more stereogenic centers of a molecule, which are cases of co-crystallization of diastereomers. [10][11][12][13][14][15][16][17] Previously, we have discovered and studied the stable co-crystallization of diastereomeric (by a sulfur atom) pinanyl sulfoxides. 17 These compounds are crystallized as H-bonded dimers, constructed by forming a new centrosymmetrical stereogenic sulfur-containing synthon F (Fig.…”

Synthesis of 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-1,4-benzoxazines from oxides of internal perfluoroolefins

“…At the same time, we have shown that the oxirane cycle can be converted into N,O,S-containing heterocycles by reactions of internal perfluoroolefin oxides with N,O,Sbifunctional nucleophilic reagents [6][7][8]. Thus, reactions between perfluoro-2,3-epoxyalkanes and nucleophiles such as ethylenediamine, 2-aminoethanol, thiourea, thiosemicarbazide and thiosemicarbazones of carbonyl compounds afforded corresponding fluoroalkyl-containing diazines, oxazines, 2-amino-and 2-hydrazinothiazolines, thiazolinylhydrazones of ketones and camphor.…”

A route to fluorocontaining N,S-heterocycles via octafluoro-2,3-epoxybutane

“…At the same time, we have shown previously that oxides of internal perfluoroolefins are excellent building blocks for synthesis of a large variety of 5,6-membered heterocycles such as diazines, quinaxolines, oxazines, benzoxazines and thiazolines [13][14][15][16]. Continuing our efforts directed towards synthesis of fluorocontaining heterocycles we report in the present paper on conversion of internal octafluoro-2,3-epoxybutane 1 (cis:trans $ 10:90) [17] into new N,S-heterocycles: bis(trifluoromethyl)dihydrobenzothiazine 2, bis(trifluoromethyl)bis(benzothiazine) 5 and trifluoromethylcontaining benzothiazolidine 6 using 2-aminothiophenol.…”