Abstract
All chemicals were supplied by Aldrich, with the exception of reagent grade acetone (supplied by Fluka), Zeoprep silica, Merck standardised alumina 90, Merck silica 9,385 (partical size 0.040–0.063 mm), and 95 % HPLC grade pentane (supplied by Romil). All chemicals were used without further purification except diethyl ether, toluene, and THF, which were dried in Grubbs solvent press and stored in Strauss flasks under a nitrogen atmosphere. All benzaldehydes (supplied by Aldrich) were checked by NMR for the presence of carboxylic acids, but no trace of acid was found and so the benzaldehydes were used without further purification. Phosphonium salts were dried in a vacuum dessicator over P2O5 and, together with KHMDS and NaHMDS, were stored in an mBraun glove box under an atmosphere of argon. Oxalyl chloride was stored under an atmosphere of nitrogen in a Young’s flask, and dispensed by nitrogen-flushed syringe. 1,2-O-isopropylidene-3-O-methyl-α-D-xylopentodialdofuranose-(1,4) was dissolved placed in a Schlenk flask under argon gas, and dissolved in dry THF to give a 0.5 mol L−1 solution. This solution was stored in the Schlenk flask under nitrogen at −18 °C in a freezer. 2-methylbenzaldehyde (o-tolualdehyde) was stored under nitrogen in a sealed Fluka® vessel.
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- 1.
Melting point is 79–81 °C.
- 2.
It was ensured that the aldehydes to be used were free of carboxylic acid by NMR analysis. Diagnostic singlets were observed at approximately 10.4 ppm for the 2-halobenzaldehydes, and at 10 ppm for benzaldehyde itself. No signals pertaining to carboxylic acid were observed.
- 3.
- 4.
Characterisation details for E-2-iodostilbene is given above in this section.
- 5.
Characterisation data for for Z-2-iodostilbene is given above in this section.
- 6.
It was ensured that the 2-methoxybenzaldehyde used was free of 2-methoxybenzoic acid by dissolving the compound in dichloromethane, and washing the dichloromethane solution with two aliquots of saturated aqueous sodium hydrogencarbonate solution. The dichloromethane phase was then dried using MgSO4, and the drying agent was removed by filtration. Evaporation of the dichloromethane first on rotary evaporator and then on the vacuum line gave the 2-methoxybenzaldehyde.
- 7.
Characterisation details for Z-2,2′-diiodostilbene are given in this section.
- 8.
Acetonylmethyldiphenylphosphorane was found to be insoluble in THF below ca. −50 °C. Addition of 2-chlorobenzaldehyde to a biphasic salt-free mixture of ylide and THF at −78 °C followed by addition of HCl at low temperature resulted in no reaction.
- 9.
For characterisation details for the Z-isomer of this compound, see Sect. 4.6.1.
- 10.
CCDC-883627 contain the X-ray crystallographic data for this compound. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.
- 11.
See Sect. 4.2.5, for characterisation details of this compound.
- 12.
Characterisation details for P-(isobutyl)-P-phenyldibenzophospholium bromide are given in Sect. 4.2.5.
- 13.
See Sect. 4.9 of this thesis for details of the characterisation of this compound.
- 14.
Characterisation data for this compound is given in Sect. 4.8.
- 15.
Characterisation data for this compound is given in Sect. 4.4.
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Byrne, P.A. (2012). Experimental. In: Investigation of Reactions Involving Pentacoordinate Intermediates. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-32045-3_4
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