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On the Effect of Backbone Modifications in 3,3‐Dimethyl‐1‐(trifluoromethyl)‐3 H ‐1λ 3 ,2‐benziodaoxole
Author(s) -
Santschi Nico,
Matthey Coraline,
Schwenk Rino,
Otth Elisabeth,
Togni Antonio
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403634
Subject(s) - chemistry , hypervalent molecule , trifluoromethyl , reagent , reactivity (psychology) , stereochemistry , computational chemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl , medicine , alternative medicine , pathology
We report on the effect of small side‐chain modifications to the structure of 3,3‐dimethyl‐1‐(trifluoromethyl)‐3 H ‐1λ 3 ,2‐benziodaoxole ( 1b ) on its reactivity, as expressed by the initial rate v 0 in a model reaction, and show how the latter can be successfully correlated to an easily determined physical parameter p , a 13 C NMR chemical shift. The relationship v 0 ~ p is already present in the simplest starting material devoid of the hypervalent bond and the iodine core and, therefore, presents an interesting approach towards the future scaffold‐optimization of this class of reagents.