US EPA

3453083 

Journal Article 

Generation of ortho-SF5-Benzyne and Its Diels-Alder Reactions with Furans: Synthesis of 1-SF5-Naphthalene, Its Derivatives, and 1,6(1,7)-Bis-SF5-naphthalenes 

Kanishchev, OS; Dolbier, WR 

2016 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

81 

22 

11305-11311 

English 

27788332 

10.1021/acs.joc.6b02276 

WOS:000391248800069 

http://://WOS:000391248800069
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Generation of ortho-SF5-benzyne was achieved by a lithiation/elimination sequence starting from 2-fluoro-SF5-benzene. The highly reactive ortho-SF5-benzyne intermediate was trapped by furan or 2-methylfuran in situ, and the obtained stable Diels-Alder adducts were subjected to the series of further chemical transformation, which led to the formation of previously unknown 1-SF5-naphthalene and its derivatives with bromo, amino, hydroxy, and methyl substituents, including bis-SF5-substituted naphthalenes. NMR spectroscopy experiments revealed characteristic through-space coupling between the SF5-group's equatorial fluorines and proton/carbon nuclei of -H, -CH3, and -OH substituents in the peri-position to the SF5-group of 1-SF5-naphthalenes.