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A study on the ability of 2,5‐dihydro‐ and 2,3,4,5‐tetrahydro‐1h‐phosphole oxides, as well as 7‐phosphanorbornene 7‐oxide derivatives to undergo uv light‐mediated fragmentation‐related phosphinylation of methanol
Author(s) -
Keglevich Gyöurgy,
Kovács János,
Szelke Helga,
Köurtvéalyesi Tamás
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430329
Subject(s) - chemistry , phosphole , zindo , mndo , photochemistry , ring strain , ring (chemistry) , fragmentation (computing) , methanol , oxide , reactivity (psychology) , medicinal chemistry , computational chemistry , organic chemistry , molecule , medicine , alternative medicine , pathology , computer science , operating system
Reactivity of the title P‐heterocycles ( 1‐14 ) in the photoinduced fragmentation‐related phosphinylation of methanol was found to be influenced by the extent of ring strain and the UV absorption at 254 nm. The 7‐phosphanorbornene oxides ( 7‐14 ) are universal precursors due to their ring strain, no matter if they are UV‐active or not at 254 nm. The easily available 2,5‐dihydro‐1 H ‐phosphole oxides can be applied only in case of 1‐phenyl substitution that enhances the absorption at 254 nm. The ring strain of representative P‐heterocycles ( 5‐8 ) was evaluated by HF/6‐31G* and B3LYP/6‐31+G* calculations. UV spectra of compounds 5‐8 were interpreted by ZINDO/S and MNDO‐d calculations. The new precursors ( 11‐14 ) made possible the extension of the phosphinylations.