Tetrahedron

Preparation of methylenedifluorocyclopropanes via cyclopropyl anion promoted β-elimination

…, Y Nakamura, M Kibashi, H Horikawa, T Taguchi

Index: Shibuya, Akira; Okada, Midori; Nakamura, Yuko; Kibashi, Mie; Horikawa, Hiroaki; Taguchi, Takeo Tetrahedron, 1999 , vol. 55, # 34 p. 10325 - 10340

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Citation Number: 15

Abstract

Preparation of methylenedifluorocyclopropanes 2 through the β-elimination reaction promoted by difluorocyclopropyl anion formed by cleavage of C Si bond with TBAF is described. Base-catalyzed isomerization of 2 to difluorocyclopropene 11 shows the latter structure themodynamically more stable in contrast to non-fluorinated cases. Application of this method to the synthesis of methylenedifluorocyclo-propylglycine (F2MCPG) derivative ...