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Reversible decomposition of mono(alpha-hydroxy)phosphines and their reaction with alpha,beta-unsaturated aldehydes

TitleReversible decomposition of mono(alpha-hydroxy)phosphines and their reaction with alpha,beta-unsaturated aldehydes
Publication TypeJournal Article
Year of Publication2009
AuthorsMoiseev, DV, Marcazzan, P, James, BR
JournalCanadian Journal of Chemistry-Revue Canadienne De Chimie
Volume87
Pagination582-590
Date PublishedApr
Type of ArticleArticle
ISBN Number0008-4042
Keywords(alpha-hydroxy)phosphines, alpha, beta-unsaturated aldehydes, CHEMISTRY, CHLORIDE, diphenylphosphine, FORMALDEHYDE, hydrophosphination, LIGNIN, NUCLEAR MAGNETIC-RESONANCE, PHOSPHONIUM CHLORIDE, TERTIARY PHOSPHINES, TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM, TRIS(HYDROXYMETHYL)PHOSPHINE, WATER
Abstract

{The mono (alpha-hydroxy) phosphines R2PCH(OH)R’ (R = Ph, R’ = H, Et, CH2Ph, Ph, p-X-C6H4; R = cyclohexyl, R’ = Ph) are prepared under solvent-free conditions by a 1:1 reaction of Ph2PH with the appropriate aldehyde, and their stabilities (with respect to reversible dissociation into reactants), studied in DMSO, Et2O, and MeOH, increase with decreased basicity of the hydroxyphosphine; for example, for the Ph2PCH (OH) C6H4-p-X phosphines, stability decreases in the order:X = CN > Cl > F > H > Me > OMe. A 1:1 room-temperature reaction of the (alpha-hydroxy) phosphines (except for R’ = H) with cinnamaldehyde in DMSO slowly yields the known mono-and di-phosphines Ph2PCH(Ph)CH2CHO (4a) and Ph2PCH(Ph)CH2CH(PPh2)OH (10a), and the corresponding R’CHO aldehyde. In MeOH, the sequentially formed intermediates
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