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Ring-opening Reaction of 2,2-Dichloro-1'-methyl-spiro [cyclopropane-1,9'-fluorene] Derivatives

Memoirs of the Faculty of Engineering, Yamaguchi University Volume 39 Issue 1 Page 143-148
published_at 1988-10
KJ00000156715.pdf
[fulltext] 410 KB
Title
2.2-ジクロロ-1'-メチルスピロ〔シクロプロパン-1.9'-フルオレン〕誘導体の開環反応
Ring-opening Reaction of 2,2-Dichloro-1'-methyl-spiro [cyclopropane-1,9'-fluorene] Derivatives
Creators Kajigaeshi Shoji
Creators Kohama Toshio
Creators Fujiwara Toshio
Creators Sone Kazuhito
Creators Nishida Akiko
Source Identifiers
The ring opening reactions of trans-2,2-dichloro-1'-methyl-spiro〔cyclopropane-1,9'-fluorene〕 derivatives 〔1〕 with silver ion in alcohols and with n-Bu_3SnH in xylene gave (Z)-9-(1-chloro ethenyl)-9-methoxy-1-methylflouorene derivatives 〔6〕 and (Z)-9-(1-chloroethenyl)-1-methyl-fluorene derivatives 〔11〕, respectively. The thermal decomposition of 〔1〕 in HCB gave (Z)-9-chloro-9-(1-chloroethenyl)-1-methylflurene derivatives 〔9〕. In any cases, 9-alkylidenefluorene dervatives (such as 〔7〕 and 〔10〕)did not obtained. That is, it turned out that 1-methyl group in flurene ring controlled the direction led the products (〔6〕, 〔9〕 and 〔11〕) from the allyl cation 〔8〕, ring opening intermediate, by its steric evidence.
Subjects
化学 ( Other)
Languages jpn
Resource Type departmental bulletin paper
Publishers 山口大学工学部
Date Issued 1988-10
File Version Version of Record
Access Rights open access
Relations
[ISSN]0372-7661
[NCID]AN00244228
Schools 工学部