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By W Parker

ISBN-10: 0851865828

ISBN-13: 9780851865829

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Sugiura, T. Matsumoto, H. Shiraharna, and H. Hashimoto, Bull. Chem Soc. Japan, 1974, 47. 1037. 24 Alicyclic Chemistry H exo MeLi-LiI + ___+ H endo Factors affecting the stereoselectivity of carbene addition to styrene and phenyl vinyl ether have also been d i ~ c u s s e d . ' ~ ~ Le Goaller and Pierre'49 have described a new route to cyclopropanediol derivatives, utilizing the addition of alkoxycarbenes (from the action of lithium alkyls on chloromethyl ethers) to enol ethers. Yields of cyclopropanediols were always low and sideproducts numerous, and efficient routes to this class of compounds remain a synthetic challenge.

Sakan. E. Sugiura, T. Matsumoto, H. Shiraharna, and H. Hashimoto, Bull. Chem Soc. Japan, 1974, 47. 1037. 24 Alicyclic Chemistry H exo MeLi-LiI + ___+ H endo Factors affecting the stereoselectivity of carbene addition to styrene and phenyl vinyl ether have also been d i ~ c u s s e d . ' ~ ~ Le Goaller and Pierre'49 have described a new route to cyclopropanediol derivatives, utilizing the addition of alkoxycarbenes (from the action of lithium alkyls on chloromethyl ethers) to enol ethers. Yields of cyclopropanediols were always low and sideproducts numerous, and efficient routes to this class of compounds remain a synthetic challenge.

Girard and J. M. Conia, Tetrahedron Letters, 1974, 3333. S. Miyano and H. Hashimoto, Bull. Chem. SOC. Japan, 1974,47, 1500. 8 % Scheme 9 Difluorocarbene can be generated by thermolysis of a trifluoromethylmercurial in the presence of sodium iodide,lW and its cycloaddition to norbornadiene has been investigated. A mixture of two products (79) and (80) is obtained, the latter evidently arising by a linear cheleotropic reaction. 14' Similar primary products are obtained from the addition of chlorofluorocarbene to norbornadiene, but here the reaction is complicated by secondary cyclopropyl-ally1 rearrangements.

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Alicyclic Chemistry Vol. 4 by W Parker


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