Synthesis of functional Δ3-1,3,5-oxazaphospholene and 2H-1,4,2-diazaphosphole complexes via catalytic ring expansion reactions of a 2H-azaphosphirene complex

Autor:	Christoph Neumann, Andrea Prehn Junquera, Peter G. Jones, Rainer Streubel, Cathleen Wismach
Rok vydání:	2003
Předmět:	Steric effects Chemistry Stereochemistry Organic Chemistry Diastereomer Cyclohexanone Ring (chemistry) Biochemistry Medicinal chemistry Catalysis Benzaldehyde chemistry.chemical_compound Elemental analysis Drug Discovery Acetone
Zdroj:	Tetrahedron. 59:6213-6220
ISSN:	0040-4020
Popis:	Catalytically-induced ring expansion of 2H-azaphosphirene complex 1 using ferrocenium hexafluorophosphate and acetone ( 2 ), diethylketone ( 3 ), cyclohexanone ( 4 ), benzaldehyde ( 5 ) or para-hydroxy-benzaldehyde ( 6 ) furnished selectively the Δ3-1,3,5-oxazaphospholene complexes 7–11 , whereas with ortho- and para-hydroxy- or ortho- and para-amino-substituted benzonitriles the 2H-1,4,2-diazaphosphole complexes 16–19 were obtained. Two further findings are noteworthy: (1) The significant decreased reaction time in the case of the sterically more demanding carbonyl derivatives 2–4 and (2) the formation of diastereomers in the case of 10 and 11 with a ratio of 8:1 and 9:1, respectively. All products were characterized by NMR, MS and elemental analysis and the configuration of complexes 7 and 10a were determined by X-ray single-crystal diffraction analysis.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3d611ef36802e771b0b677bcfef262c2 https://doi.org/10.1016/s0040-4020(03)01044-5 Zobrazit plný text záznamu Full Text from ScienceDirect