Anomalous reaction of pentafluorophenacyl bromide with hexamethylenetetramine. Structure of the product

RA Henry, RA Hollins, C Lowe-Ma…

Index: Henry, Ronald A.; Hollins, Richard A.; Lowe-Ma, Charlotte; Moore, Donald W.; Nissan, Robin A. Journal of Organic Chemistry, 1990 , vol. 55, # 6 p. 1796 - 1801

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Citation Number: 13

Abstract

The title compounds condense in chloroform to yield tetrafluorobenzo [b]-l, 3, 5, 7- tetraazatetracyclo-[7.3. 13~ 7.1 s~ 9.01~ 9] tetradecan-10-one (l), a reaction proposed to involve both an ortho fluorine elimination and two Stevens type rearrangements. Structural assignment of the fluorescent product was based upon'H, 13C, 19F, and 15N NMR spectra and a complete X-ray crystallographic determination. Additional studies supported the ...