Conformational Analysis of the 1,3‐Oxaphosphorinanes Formed from α,β‐Unsaturated Aldehydes and the (Hydroxymethyl)phosphines RP(CH2OH)2 (R = Ph or CH2OH)
Abstract:Equimolar reactions of cinnamaldehyde or its 3,5‐dimethoxy‐4‐hydroxy derivative (sinapaldehyde) with RP(CH2OH)2 (R = Ph or CH2OH) were studied in MeOH or CD3OD at room temperature by NMR spectroscopy. In MeOH, nucleophilic attack of the phosphine at the CC bond, with concomitant loss of CH2O, affords the tertiary phosphine HOCH2P(R)CH(Ar)CH2CHO (3) that rapidly converts mainly into a 1,3‐oxaphosphorinane derivative (5) formed as a mixture of four diastereomers. Conformational analysis reveals that the Ar grou… Show more
“…Likely the formation of L1 goes via a 1,3-oxaphosphorinane hemiacetal intermediate which is similar to compounds observed from the reaction between THP and cinnamaldehyde. 24…”
Section: Resultsmentioning
confidence: 99%
“…Likely the formation of L1 goes via a 1,3-oxaphosphorinane hemiacetal intermediate which is similar to compounds observed from the reaction between THP and cinnamaldehyde. 24 L1 can be obtained in one-pot in moderate yield (56%). It was easily purified by removing unconverted THP and THPC with an aqueous wash, followed by flash column chromatography that can be carried out in air.…”
“…Likely the formation of L1 goes via a 1,3-oxaphosphorinane hemiacetal intermediate which is similar to compounds observed from the reaction between THP and cinnamaldehyde. 24…”
Section: Resultsmentioning
confidence: 99%
“…Likely the formation of L1 goes via a 1,3-oxaphosphorinane hemiacetal intermediate which is similar to compounds observed from the reaction between THP and cinnamaldehyde. 24 L1 can be obtained in one-pot in moderate yield (56%). It was easily purified by removing unconverted THP and THPC with an aqueous wash, followed by flash column chromatography that can be carried out in air.…”
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