Synthesis and fragmentation of new 2-phosphabicyclo[2.2.2]octene 2-oxides

✍ Scribed by György Keglevich; Helga Szelke; Annamária Tamás; Veronika Harmat; Krisztina Ludányi; Ágnes Gyöngyvér Vaskó; László Tőke

• Book ID: 102230809
• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 135 KB
• Volume: 13
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.10052

✦ Synopsis

Abstract

The substitution pattern of the 2‐phosphabicyclo[2.2.2]octene framework and the skeleton itself were varied to obtain new cycloadducts usable in phosphorylations and to study their ability to undergo fragmentation. Thus, an N‐methyl and several P‐trialkylphenyl derivatives (7 and 9, respectively) were synthesized, together with two diaza species (8) whose stereostructure was evaluated by single crystal X‐ray analysis. Mechanistic studies on the UV light‐mediated photolysis of the P‐aryl phosphabicyclooctenes (9) in the presence of methanol supports the suggestion of a novel addition–elimination reaction path. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:626–632, 2002; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10052