gem-Dimethylcyclopropanation of dibenzylideneacetone using triisopropyl sulfoxonium tetrafluoroborate

Michael G. Edwards; David S. Pugh; Adrian C. Whitwood; Richard J. K. Taylor

doi:10.1107/S0108270108042431

gem-Dimethylcyclopropanation of dibenzylideneacetone using triisopropyl sulfoxonium tetrafluoroborate

Michael G. Edwards, David S. Pugh, Adrian C. Whitwood, Richard J. K. Taylor

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The reaction between dibenzylideneacetone (dba) and triisopropyl sulfoxonium tetrafluoroborate has been reinvestigated. The stereochemistry of the major diasteromeric bis(gem-dimethylcyclopropane) adduct has now been assigned as [(1RS,3RS)-2,2-dimethyl-3-phenylcyclopropyl][(1SR,3SR)2,2-dimethyl-3-phenylcyclopropyl] methanone, C23H26O, by X-ray crystallographic studies on a twinned crystal. The asymmetric unit contains two molecules of the adduct, the conformations of which differ in the orientation of the phenyl ring relative to the adjacent cyclopropanated double bond. The carbonyl groups of each adduct are aligned approximately along the a axis and in opposite directions to each other. The molecules pack to give a sinusoidal pattern along the b axis. This is the first acyclic bis(dimethylcyclopropyl) ketone for which an X-ray crystal structure determination has been reported, and is also the first bis-cyclopropanated dba analogue. The knowledge that the major diastereomer has the meso structure (and therefore the confirmation that the minor isomer is the racemate) will prove invaluable in future studies to utilize bis(dimethylcyclopropyl) ketones as reagents, in rearrangement processes, and as potential ligands and ligand precursors in organometallic chemistry.

Original language	English
Pages (from-to)	O39-O41
Number of pages	3
Journal	ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS
Volume	65
Issue number	2
DOIs	https://doi.org/10.1107/S0108270108042431
Publication status	Published - Feb 2009

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title = "gem-Dimethylcyclopropanation of dibenzylideneacetone using triisopropyl sulfoxonium tetrafluoroborate",

abstract = "The reaction between dibenzylideneacetone (dba) and triisopropyl sulfoxonium tetrafluoroborate has been reinvestigated. The stereochemistry of the major diasteromeric bis(gem-dimethylcyclopropane) adduct has now been assigned as [(1RS,3RS)-2,2-dimethyl-3-phenylcyclopropyl][(1SR,3SR)2,2-dimethyl-3-phenylcyclopropyl] methanone, C23H26O, by X-ray crystallographic studies on a twinned crystal. The asymmetric unit contains two molecules of the adduct, the conformations of which differ in the orientation of the phenyl ring relative to the adjacent cyclopropanated double bond. The carbonyl groups of each adduct are aligned approximately along the a axis and in opposite directions to each other. The molecules pack to give a sinusoidal pattern along the b axis. This is the first acyclic bis(dimethylcyclopropyl) ketone for which an X-ray crystal structure determination has been reported, and is also the first bis-cyclopropanated dba analogue. The knowledge that the major diastereomer has the meso structure (and therefore the confirmation that the minor isomer is the racemate) will prove invaluable in future studies to utilize bis(dimethylcyclopropyl) ketones as reagents, in rearrangement processes, and as potential ligands and ligand precursors in organometallic chemistry.",

author = "Edwards, {Michael G.} and Pugh, {David S.} and Whitwood, {Adrian C.} and Taylor, {Richard J. K.}",

year = "2009",

month = feb,

doi = "10.1107/S0108270108042431",

language = "English",

volume = "65",

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T1 - gem-Dimethylcyclopropanation of dibenzylideneacetone using triisopropyl sulfoxonium tetrafluoroborate

AU - Edwards, Michael G.

AU - Pugh, David S.

AU - Whitwood, Adrian C.

AU - Taylor, Richard J. K.

PY - 2009/2

Y1 - 2009/2

N2 - The reaction between dibenzylideneacetone (dba) and triisopropyl sulfoxonium tetrafluoroborate has been reinvestigated. The stereochemistry of the major diasteromeric bis(gem-dimethylcyclopropane) adduct has now been assigned as [(1RS,3RS)-2,2-dimethyl-3-phenylcyclopropyl][(1SR,3SR)2,2-dimethyl-3-phenylcyclopropyl] methanone, C23H26O, by X-ray crystallographic studies on a twinned crystal. The asymmetric unit contains two molecules of the adduct, the conformations of which differ in the orientation of the phenyl ring relative to the adjacent cyclopropanated double bond. The carbonyl groups of each adduct are aligned approximately along the a axis and in opposite directions to each other. The molecules pack to give a sinusoidal pattern along the b axis. This is the first acyclic bis(dimethylcyclopropyl) ketone for which an X-ray crystal structure determination has been reported, and is also the first bis-cyclopropanated dba analogue. The knowledge that the major diastereomer has the meso structure (and therefore the confirmation that the minor isomer is the racemate) will prove invaluable in future studies to utilize bis(dimethylcyclopropyl) ketones as reagents, in rearrangement processes, and as potential ligands and ligand precursors in organometallic chemistry.

AB - The reaction between dibenzylideneacetone (dba) and triisopropyl sulfoxonium tetrafluoroborate has been reinvestigated. The stereochemistry of the major diasteromeric bis(gem-dimethylcyclopropane) adduct has now been assigned as [(1RS,3RS)-2,2-dimethyl-3-phenylcyclopropyl][(1SR,3SR)2,2-dimethyl-3-phenylcyclopropyl] methanone, C23H26O, by X-ray crystallographic studies on a twinned crystal. The asymmetric unit contains two molecules of the adduct, the conformations of which differ in the orientation of the phenyl ring relative to the adjacent cyclopropanated double bond. The carbonyl groups of each adduct are aligned approximately along the a axis and in opposite directions to each other. The molecules pack to give a sinusoidal pattern along the b axis. This is the first acyclic bis(dimethylcyclopropyl) ketone for which an X-ray crystal structure determination has been reported, and is also the first bis-cyclopropanated dba analogue. The knowledge that the major diastereomer has the meso structure (and therefore the confirmation that the minor isomer is the racemate) will prove invaluable in future studies to utilize bis(dimethylcyclopropyl) ketones as reagents, in rearrangement processes, and as potential ligands and ligand precursors in organometallic chemistry.

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gem-Dimethylcyclopropanation of dibenzylideneacetone using triisopropyl sulfoxonium tetrafluoroborate

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