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P-Cl bond-induced lactamization of 2(2 '-hydroxyl)-phenyloxazoline to form a cyclic phosphinite, 3-(2-chloroethyl)-2-phenyl-2H-benzo[e][1,3,2]oxazaphosphinin-4(3H)-one: synthesis, structural studies and transition metal complexes

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Title P-Cl bond-induced lactamization of 2(2 '-hydroxyl)-phenyloxazoline to form a cyclic phosphinite, 3-(2-chloroethyl)-2-phenyl-2H-benzo[e][1,3,2]oxazaphosphinin-4(3H)-one: synthesis, structural studies and transition metal complexes
 
Creator CHAUBEY, B
MOBIN, SM
BALAKRISHNA, MS
 
Subject CATALYZED ENANTIOSELECTIVE HYDROGENATION
ASYMMETRIC HYDROGENATION
OXAZOLINE LIGANDS
ETHYLENE OLIGOMERIZATION
PHOSPHORUS LIGANDS
CHEMISTRY
REARRANGEMENT
ALKENES
DERIVATIZATION
DIPHOSPHINITE
 
Description The equimolar reaction between 2(2'-hydroxy)phenyloxazoline (1) and PPhCl2 in the presence of triethylamine afforded an unexpected cyclic product, phenyl-benzo-oxazaphosphininone (2), instead of a simple phosphinite derivative A. A similar reaction between 1 and PPhCl2 in 2 : 1 ratio also yielded the same product 2, but with one equivalent of 2(2'-hydroxy) phenyloxazoline (1) left unreacted. The formation of the cyclic product 2 is due to the P-Cl bond induced oxazoline ring opening followed by the formation of a six-membered gamma-lactam type product, 3-(2-chloroethyl)-2-phenyl-2H-benzo[e][1,3,2] oxazaphosphinin-4(3H)-one (2 also referred to as L). The reactions of 2 with H2O2, elemental sulphur or elemental selenium yielded the corresponding chalcogenides, LE (3, E = O; 4, E = S; 5, E = Se) in quantitative yield. Treatment of 2 with [Ru(eta(6)-Cymene)Cl-2](2), [Pd(COD)Cl-2] and [Pd(eta(3)-C3H5)Cl](2) resulted in the formation of [RuCl2(eta(6)-cymene)(L)] (6), [PdCl2{L}(2)] (7), and [Pd(eta(3)-C3H5)Cl(L)] (8), respectively. The compound 2 obtained in the 2 : 1 reaction when treated with [Pd(eta(3)-C3H5)Cl](2) gave the same palladium complex 8 (referred to as 9a), but co-crystallized with bis(oxazolyl)palladacycle (9b) as confirmed by single crystal X-ray analysis.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-12-28T12:10:11Z
2014-12-28T12:10:11Z
2014
 
Type Article
 
Identifier DALTON TRANSACTIONS, 43(2)584-591
1477-9226
1477-9234
http://dx.doi.org/10.1039/c3dt52223g
http://dspace.library.iitb.ac.in/jspui/handle/100/16453
 
Language English