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An Original Approach to the Synthesis of Phosphorus‐Carbon Heterocycles − The 3‐Oxo‐2,3‐dihydro‐1,3‐oxaphospholes
Author(s) -
Virieux David,
Ciptadi Ciptadi,
Bekro YvesAlain,
Cristau HenriJean
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400179
Subject(s) - chemistry , dihedral angle , phosphorus , alkyl , medicinal chemistry , carbon fibers , organic chemistry , molecule , hydrogen bond , materials science , composite number , composite material
The synthesis of new highly functionalized phosphorus heterocycles, the 3‐oxo‐2,3‐dihydro‐1,3‐oxaphospholes, was achieved by a cyclization reaction involving malonic enolates as 1,3‐ O , C ‐dinucleophiles and phosphorus compounds, such as (chloromethyl)phosphinic chlorides or alkyl (chloromethyl)phosphonochloridates, as 1,2‐dielectrophiles. Owing to the structural restriction that results from the cyclic structure, the 1 H NMR spectra reveal extreme values of 2 J P,H coupling constants that are sensitive to the HCPO dihedral angle. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)