2‐Ethyl‐2‐phosphabicyclo[2.2.2]oct‐7‐ene derivatives: Synthesis and use in fragmentation‐related phosphorylations

A 2‐phosphabicyclo[2.2.2]oct‐7‐ene oxide ( 2 ) and a 2‐phosphabicyclo[2.2.2]octa‐5,7‐diene oxide ( 3 ) with ethyl substituent on the phosphorus atom was synthesized and their fragmentation properties were studied. The phosphabicyclooctadiene oxide ( 3 ) could be utilized in both the UV light‐mediated phosphorylation of simple alcohols and in the thermoinduced phosphorylation of hydroquinone giving an easy access to P‐ethylphosphinates (e.g., 4 and 6 ). The phosphabicyclooctene oxide ( 2 ) was, however, not useful in photoinduced phosphorylations; under such conditions the precursor ( 2 ) underwent dechlorination to afford 5 . © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:196–199, 2005; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20093