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Front Cover: Borosilicate Activation of (Difluoroiodo)toluene in the gem ‐Difluorination of Phenyldiazoacetate Derivatives (Eur. J. Org. Chem. 27/2016)
Author(s) -
Sinclair Geoffrey S.,
Tran Richard,
Tao Jason,
Hopkins W. Scott,
Murphy Graham K.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201670271
Subject(s) - borosilicate glass , chemistry , hypervalent molecule , toluene , fluoride , reagent , trihalide , boron , photochemistry , inorganic chemistry , halide , organic chemistry
The cover picture shows the proposed sequence of events for the borosilicate glass‐activated gem ‐difluorination of phenyl diazoacetate using the hypervalent iodine reagent (difluoroiodo)toluene (TolIF 2 ). Progress from diazo to gem ‐difluoride involves two distinct fluorination events and the evolution of nitrogen gas. Quantum chemical calculations of a borosilicate‐like cluster show that the boron atom is sufficiently Lewis‐acidic so as to spontaneously abstract fluoride from TolIF 2 . The role of borosilicate glassware, which is the most effective activator discovered to date, was confirmed experimentally. Details are discussed in the Communication by W. S. Hopkins, G. K. Murphy et al. on p. 4603 ff .