Publication

Ring opening of gem-dihalocyclopropanes: novel types of 1,4-elimination reactions

Manfred Schlosser
1990
Journal Articles

Abstract

On treatment with Bu4N+ F-, cyclopropanecarboxylates I (R = Cl; R1 = Cl, F; R2 = OCMe3) undergo Cl-F exchange via cyclopropene intermediates. As a byproduct, H2C:CMeC.tplbond.CCO2CMe3 (II) is formed. I (R = R1 = Cl, R2 = CO2CMe3), II, and Me2CClC.tplbond.CCO2CMe3 are obtained when Me2C:CHCO2CMe3 is allowed to react with CHCl3 in strongly alk. medium. I (R = R1 = F, R2 = H) can be generated by oxidn. of the alc. In the presence of any base, however, instantaneous ring opening and dehydrofluorination occurs to give H2C:CMeCF:CHCHO. The solvolysis of 2,2-difluoro-3,3-dimethylcyclopropylmethyl p-toluenesulfonate in boiling aq. dioxane affords two ring opened products, 3,3-difluoro-2-methyl-1,4-pentadiene and 3,3-difluoro-2-methyl-4-penten-2-ol, besides 2,2-difluoro-3,3-dimethyl-1-cyclopropylmethanol. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/3ec9ab01-3a00-483b-9773-4f2bde39cdf4

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Manfred Schlosser
1990
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/3ec9ab01-3a00-483b-9773-4f2bde39cdf4

About this result

Related concepts (12)

Ring-opening polymerization

In polymer chemistry, ring-opening polymerization (ROP) is a form of chain-growth polymerization, in which the terminus of a polymer chain attacks cyclic monomers to form a longer polymer (see figure). The reactive center can be radical, anionic or cationic. Some cyclic monomers such as norbornene or cyclooctadiene can be polymerized to high molecular weight polymers by using metal catalysts. ROP is a versatile method for the synthesis of biopolymers. Ring-opening of cyclic monomers is often driven by the relief of bond-angle strain.

Ring (mathematics)

In mathematics, rings are algebraic structures that generalize fields: multiplication need not be commutative and multiplicative inverses need not exist. In other words, a ring is a set equipped with two binary operations satisfying properties analogous to those of addition and multiplication of integers. Ring elements may be numbers such as integers or complex numbers, but they may also be non-numerical objects such as polynomials, square matrices, functions, and power series.

Cyclic compound

A cyclic compound (or ring compound) is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon (i.e., are carbocycles), none of the atoms are carbon (inorganic cyclic compounds), or where both carbon and non-carbon atoms are present (heterocyclic compounds with rings containing both carbon and non-carbon).