172989-55-8Relevant academic research and scientific papers
Palladium(II)-promoted cyclization reaction of 4-hydroxybutyronitrile to 2-Iminotetrahydrofuran. X-ray structure of cis-PdCl2{N(H)=CCH2CH2CH 2O}-(PPh3)·1/2CH2Cl2
Bertani, Roberta,Gotti, Marta,Michelin, Rino A.,Mozzon, Mirto,Bandoli, Giuliano,Angelici, Robert J.
, p. 1236 - 1241 (1996)
Reaction of 3-bromo-1-propanol with Et4N(CN) in CH2Cl2 at room temperature gives in high yield 4-hydroxybutyronitrile, HO(CH2)3CN (1), which upon reaction with Na2PdCl4 affords [PdCl2{N(H)=CCH2CH2CH2O} 2] (2), containing two 2-iminotetrahydrofuran ligands derived from intramolecular cyclization of 1. Substitution of one imino ligand for an entering nucleophile L leads to the complexes [PdCl2{N(H)=CCH2CH2CH20}(L)] (L = PPh3 (3), py (4), DMF (5)). Similarly, the reaction of 2 with 1 equiv of cis-Ph2PCH=CHPPh2 results in the displacement of the two iminolactone ligands and formation of [PdCl2(Ph2PCH=CHPPh2)]. The ligand 1 and the complexes 2-5 were characterized by analytical and spectroscopic techniques. IR data suggest that 2 and 3 are present as a mixture of cis and trans isomers, while 4 and 5 have a trans stereochemistry. Complex 3 gave crystals of the cis form, as evidenced by an X-ray structural determination.
