The Nucleophilic Ring-opening Reactions of α,α′-Dinitrocycloalkanones

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概要

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• The keto and enolic characters of 2,6-dinitrocyclohexanone (<B>1</B>), 2,6-dinitro-4-methylcyclohexanone (<B>2</B>), and 2,7-dinitrocycloheptanone (<B>3</B>) were spectroscopically investigated and discussed. It was found that the reactions of <B>1</B> and <B>2</B> with nucleophiles can take either of two courses, depending upon the nucleophiles used: (a) the addition to the enol carbon or carbonyl carbon of the keto form, followed by ring-opening giving 2,6-dinitro- and 2,6-dinitro-4-methyl-hexanoates respectively; (b) the abstraction of the 2- and 6-protons, followed by the formation of the corresponding di-<I>aci</I>-nitronates. Primary alkoxide ions belong to the (a) group, whereas secondary and tertiary alkoxide ions, NH<SUP>−</SUP><SUB>2</SUB>, RHN<SUP>−</SUP>, and AcO<SUP>−</SUP>, belong to the (b) group. The IR and UV spectra of the resultant α,ω-dinitrocarboxylic acid esters were also discussed.

• 公益社団法人 日本化学会の論文

著者

• Kobayashi Yoshinari

  Nagoya Research Laboratory, Chemicals Research and Development Laboratories, Toray Industries, Inc.

• Kobayashi Yoshinari

  Nagoya Research Laboratory, Chemicals and Development Laboratories, Toray Industries, Inc.

関連論文

• The Nucleophilic Ring-opening Reactions of α,α′-Dinitrocycloalkanones

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