Synthesis 2012; 44(14): 2155-2161
DOI: 10.1055/s-0031-1290776
special topic
© Georg Thieme Verlag Stuttgart · New York

Lewis Acid Promoted Reactions of 1,1-Diarylallenes and Ketone Derivatives: Synthesis of Indenes by an Addition/Cyclization Reaction

Shoko Yamazaki*
a  Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan
,
Yugo Fukushima
a  Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan
b  Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka 599-8531, Japan, Fax: +81(742)279289   Email: yamazaks@nara-edu.ac.jp
,
Tetsuma Ukai
a  Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan
,
Kohei Tatsumi
a  Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan
,
Akiya Ogawa
b  Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka 599-8531, Japan, Fax: +81(742)279289   Email: yamazaks@nara-edu.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 19 December 2011

Accepted: 01 March 2012

Publication Date:
03 April 2012 (eFirst)

Abstract

The Lewis acid promoted reaction of 1,1-diarylallenes with ketone derivatives was examined. The tin(IV) chloride promoted reaction of diarylallenes with vinyl ketones gave indene derivatives through a conjugate addition/cyclization reaction. The reaction of diphenylallene with diethyl oxomalonate in the presence of one equivalent of tin(IV) chloride at –40 °C gave diethyl hydroxy(3-phenyl-1H-inden-2-yl)malonate as the major product through a carbonyl addition/cyclization reaction, whereas the same reactants in the presence of 0.2 equivalents of tin(IV) chloride at 80 °C gave diethyl (3-phenyl-1H-inden-2-yl)malonate. Diethyl hydroxy(3-phenyl-1H-inden-2-yl)malonate was also converted into the latter product on heating at 80 °C in the presence of 0.2 equivalents of tin(IV) chloride.

Supporting Information

 
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