2014
DOI: 10.1002/jhet.2280
|View full text |Cite
|
Sign up to set email alerts
|

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 CC 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

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1

Citation Types

0
2
0

Year Published

2016
2016
2023
2023

Publication Types

Select...
4

Relationship

0
4

Authors

Journals

citations
Cited by 4 publications
(2 citation statements)
references
References 28 publications
0
2
0
Order By: Relevance
“…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%
See 1 more Smart Citation
“…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.…”
Section: Ligand Synthesismentioning
confidence: 99%