A post-scriptum on fluorine…

Hi all, I am glad that one of the readers reminded me about a classic work by Jack Dunitz. In addition to my personal response, I decided to post a link so that everyone can see it and save in their folders of “important papers”. 

http://onlinelibrary.wiley.com/doi/10.1002/chem.19970030115/abstract

The title says it all: a contradiction to what the Linclau study suggests. However, the Dunitz paper is primarily a crystallographic study, which is an important distinction. One comment: people no longer come up with really great titles. There is a monumental inscription in the title of the Dunitz contribution: “Organic Fluorine Hardly Ever Accepts Hydrogen Bonds”! 

 

2 thoughts on “A post-scriptum on fluorine…

  1. there is one unusual property of prefluoroalkyl iodides: not only they are completely non-electrophilic towards common nucleophiles (but they react rapidly with phospines, by radical mechanism), they also form stable complexes with nucleophilic amines via iodine – nitrogen bond, i.e. CF3CF2I.DABCO

  2. Yes, that’s right – attack can be at halogen. I love using this example when describing Sn2 reactions and how they can go “south” upon H-to-F substitution.

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