000081581 001__ 81581
000081581 005__ 20180127194635.0
000081581 037__ $$aARTICLE
000081581 245__ $$aHydrogen fluoride abstraction from vicinal difluoroalkanes: reaction conditions and syn/anti-stereoselectivity
000081581 260__ $$c1988
000081581 269__ $$a1988
000081581 336__ $$aJournal Articles
000081581 500__ $$aCAN 110:94223
000081581 500__ $$a22-4
000081581 500__ $$aPhysical Organic Chemistry
000081581 500__ $$aInst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
000081581 500__ $$aJournal
000081581 500__ $$a0040-4020
000081581 500__ $$awritten in English.
000081581 500__ $$a119105-48-5 (5-Nonyl fluoride) Role: RCT (Reactant), RACT (Reactant or reagent) (attempted dehydrofluorination of); 119105-44-1; 119105-45-2 Role: RCT (Reactant), RACT (Reactant or reagent) (dehydrofluorination of, stereochem. in mechanism of); 7664-39-3 Role: PRP (Properties) (dehydrofluorination, of difluoroalkanes, mechanism of); 6975-99-1P (6-Dodecyne); 119105-46-3P; 119105-47-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
000081581 520__ $$avic-Difluoroalkanes are as inert as monofluoroalkanes toward NaOMe in MeOH. Stronger bases, however, can perform dehydrofluorinations relatively smoothly. KOCMe3 in THF at 75 Deg acts exclusively by an antiperiplanar process: meso- and dl-6,7-difluorododecane are converted to (E)- and (Z)-6-fluoro-6-dodecene, resp. Lithium diisopropylamide was an extremely powerful eliminating reagent when employed in hexane, while its reactivity is considerably diminished in di-Et ether and has almost completely vanished in THF. This solvent effect together with the loss of stereoselectivity points at an electrophilic assistance as the key event in lithium amide-induced dehydrofluorinations. [on SciFinder (R)]
000081581 6531_ $$aStereochemistry (of dehydrofluorination of difluoroalkanes); Kinetics of dehydrofluorination (of difluoroalkanes); Dehydrofluorination (of difluoroalkanes
000081581 6531_ $$amechanism of); Alkanes Role: RCT (Reactant)
000081581 6531_ $$aRACT (Reactant or reagent) (fluoro
000081581 6531_ $$adehydrofluorinat
000081581 6531_ $$adehydrofluorination difluoroalkane kinetics stereochemistry; difluoroalkane dehydrofluorination kinetics stereochemistry
000081581 700__ $$aMatsuda, Hiroyuki
000081581 700__ $$aHamatani, Takeshi
000081581 700__ $$aMatsubara, Seijiro
000081581 700__ $$0240930$$aSchlosser, Manfred$$g123541
000081581 773__ $$j44$$k10$$q2865-74$$tTetrahedron
000081581 909C0 $$0252181$$pLSCO
000081581 909CO $$ooai:infoscience.tind.io:81581$$particle
000081581 937__ $$aLSCO-ARTICLE-1988-005
000081581 970__ $$a194/LSCO
000081581 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000081581 980__ $$aARTICLE