Rearrangement of fluorinated methylenecyclopropane

✍ Scribed by A. Skancke; L.J. Schaad; B.A. Hess Jr.

• Book ID: 104151014
• Publisher: Elsevier Science
• Year: 1989
• Tongue: English
• Weight: 32 KB
• Volume: 45
• Category: Article
• ISSN: 0022-1139
• DOI: 10.1016/s0022-1139(00)84501-7

✦ Synopsis

We have recently reported on a novel, one-step mechantsm for the degenerate thermal rearrangement of methylenecyclopropane [l]. This is an alternative to the two-step process previously reported.

By monosubstitution of the hydrocarbon we obtain two ditferent modes of ring closure, syn or anti with respect to the substttuent. Presently we have studied the reaction On the basis of ah inttfocalculations on the level MP2(6-31G*)//3-21G. it is concluded that in a reaction mechanism parallelhng the hydrocarbon system, the ring closure is an0 to the fluorine.