Selective skeletal rearrangement of tricyclo[5.4.0.01,5]undecanes to Tricyclo[5.3.1.01,5]-and [5.4.0.03,8]undecanes

Kiyomi Kakiuchi*, Shuichi Kumanoya, Kazuya Kobiro, Tobe Yoshito, Yoshinobu Odaira

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

An acid-catalyzed rearrangement of tricyclo-[5.4.0.01,5]undecan-11-one gave tricyclo[5.3.1.01,5]undecan-11-one in a nonnucleophilic media and tricyclo[5.4.0.03,8]un-decane-7, 8-diol in the presence of a nucleophile, respectively. Tricyclo[5.4.0.01,5]undecan-11-ols also rearranged to tricyclo-[5.4.0.03,8]undecan-7-ol. A reductive rearrangement with a hydride transfer of the alcohol gave only tricyclo[5.4.0.03,8]un-decane.

Original languageEnglish
Pages (from-to)3358-3360
Number of pages3
JournalBulletin of the Chemical Society of Japan
Volume63
Issue number11
DOIs
StatePublished - 1 Nov 1990

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