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- W2500721802 abstract "This chapter discusses the synthesis and spatial geometry of cyclopentane compounds. Several methods employed for the formation of five-membered rings are ring-contraction, ring-expansion, and some miscellaneous cyclizations. Cyclopentenes are obtained by thermal or photolytic rearrangement of cyclopropylacrylic esters and 2-cyclopropyl-1-phenylethylenes. Thermolysis of bicyclo[2,1,0]pentanes as, for example, in the formation of 1-acetyl-1,2-dimethylcyclopent-2-ene and 1-acetyl-2,3-dimethylcyclopent-2-ene also leads to cyclopentenes. The cyclopentyl cation can be generated in highly acidic solvents by hydride abstraction from cyclopentane. Spirocyclopentenes are prepared by ring-expansion of a cyclopentadienyl cyclopropanol and by malonic ester cyclization of 1,1-dimethylolcyclopent-3-ene ditoluene-p-sulfonate. The cycloaddition of electrophilic olefins to enamines of cyclopentanealdehyde offers a convenient method for the formation of [4,3]spiro derivatives. The Diels–Alder reactions of cyclopentadiene are reviewed and the factors affecting the endo/exo ratios of the products formed are discussed. The aromaticity of the cyclopentadienide anion is demonstrated by typical electrophilic substitution in methylation reactions. Where the basicity of the cyclopentadienide anion is lowered, by the introduction of electronegative groups, more strongly acidic conditions can be used as in the bromination, nitration, and acetylation of the tetracyanocyclopentadienide anion." @default.
- W2500721802 created "2016-08-23" @default.
- W2500721802 creator A5048589021 @default.
- W2500721802 date "1975-01-01" @default.
- W2500721802 modified "2023-09-25" @default.
- W2500721802 title "The Cyclopentane Group" @default.
- W2500721802 doi "https://doi.org/10.1016/b978-044453346-3.50090-1" @default.
- W2500721802 hasPublicationYear "1975" @default.
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