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Base-promoted elimination of hydrogen fluoride from alkyl fluorides : Reactivity and stereochemistry

✍ Scribed by Seijiro Matsubara; Hiroyuki Matsuda; Takeshi Hamatani; Manfred Schlosser

Book ID
104207281
Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
669 KB
Volume
44
Category
Article
ISSN
0040-4020

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✦ Synopsis

llte alcoholate-promoted dehydrohalogenation of 5-nonyl fluoride and cyclododecyl fluoride, typical straight-chain and, respectively, medium-size cyclic substrates, lea& to cis-and trans-alkenes in an approximate ratio of I : 3. With bulky bases such as lithium diisopropylamide the tram isomer may be obtained almost txelusively. In general, the elimination of hydrogen fluoride proceeds very slowly. Increase of the base strength has only a moderate effect on the rates. Electrophilic assistance as provided by lithium cations in media of low polar@ can, howevet considerably

accelerate the reaction. -Cyclodo#ecyl fluoride cannot be prepared from cyclododecanol.

It is, however, readily accessible by bromojluorination of cyclodecene and subsequent reduction of the adduct with stannane.

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