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A One‐Pot Synthesis of 1,3‐Dihydro‐1,3,3‐tris(perfluoroalkyl)isobenzofuran‐1‐olates and Their Complete NMR Spectroscopic Analysis on the Basis of 1D and 2D Experiments
Author(s) -
Tyrra Wieland,
Scherer Harald,
Babadzhanova Lesya A.,
Kirij Natalya V.,
Yagupolskii Yurii L.,
Naumann Dieter,
Pantenburg Ingo
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890019
Subject(s) - chemistry , isobenzofuran , tris , trimethylsilyl , trifluoromethyl , reagent , medicinal chemistry , alkyl , fluoride , stereochemistry , organic chemistry , inorganic chemistry , biochemistry
A convenient synthesis of the 1,3‐dihydro‐1,3,3‐tris(perfluoroalkyl)isobenzofuran‐1‐ols 3a , b was elaborated starting from commercially available phthaloyl dichloride and trimethyl(perfluoroalkyl)silanes (Me 3 SiR f ) 1a , b (R f =CF 3 , C 2 F 5 ) in the presence of a fluoride source ( Schemes 1 and 3 ). In a reaction analogous to alkyl Grignard reagents, double chloride substitution by two perfluoroalkyl groups and subsequent addition of one perfluoroalkyl group with concomitant ring closure led to this new class of compounds ( Scheme 2 ). The syntheses of the alcohols and some alcoholates, as well as of the corresponding trimethylsilyl ethers are described. A combination of special 1D and 2D NMR experiments allowed the assignment of all atoms of the new compounds. The solid‐state structure of 1,3‐dihydro‐1,3,3‐tris(trifluoromethyl)isobenzofuran‐1‐ol ( 3a ) was elucidated by X‐ray diffraction methods.