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

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...

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Published inSynthesis (Stuttgart) Vol. 44; no. 14; pp. 2155 - 2161
Main Authors Yamazaki, Shoko, Fukushima, Yugo, Ukai, Tetsuma, Tatsumi, Kohei, Ogawa, Akiya
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.07.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
cyclizations
allenes
ORGANIC-SYNTHESIS
CATALYZED REACTIONS
ARYLVINYLIDENECYCLOPROPANES
Michael additions
addition reactions
Lewis acids
PROTOCOL
ACETALS
ketones
CYCLIZATION
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Summary: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 degrees 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 degrees 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 degrees C in the presence of 0.2 equivalents of tin(IV) chloride.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0031-1290776