2007
DOI: 10.1021/jo061946f
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Synthesis, Mechanism of Formation, and Dynamics of a Highly Fluorinated Methylenecyclobutene

Abstract: Treatment of the hydrazone of 2H-perfluoro-2-methyl-3-pentanone with triethylamine at elevated temperatures yields a methylenecyclobutene via degradation to an acetylene followed by dimerization. The dimerization occurs even at -78 degrees C, and details of the reaction pathway have been elucidated. Both the acidity and the conformational dynamics of the methylenecyclobutene are influenced by buttressing effects in this crowded molecule.

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Cited by 3 publications
(1 citation statement)
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“…Furin et al have reported that treatment of perfluoro-2-methyl-2-pentene ( 1 ) with hydrazine hydrate in acetic acid yields hydrazone 2 as a 2.1:1 mixture of Z - and E -isomers, respectively, characterized by 1 H, 13 C, and 19 F NMR spectra . We repeated the preparation of 2 to study the interesting transformation it undergoes upon treatment with triethylamine . In the course of that investigation, we observed in the hydrazone striking behavior that became the subject of this report.…”
Section: Introductionmentioning
confidence: 73%
“…Furin et al have reported that treatment of perfluoro-2-methyl-2-pentene ( 1 ) with hydrazine hydrate in acetic acid yields hydrazone 2 as a 2.1:1 mixture of Z - and E -isomers, respectively, characterized by 1 H, 13 C, and 19 F NMR spectra . We repeated the preparation of 2 to study the interesting transformation it undergoes upon treatment with triethylamine . In the course of that investigation, we observed in the hydrazone striking behavior that became the subject of this report.…”
Section: Introductionmentioning
confidence: 73%