New 7-phosphanorbornenes derived from 2-methyl-1-phenyl- And 1-cyclohexyl-3-methyl-2,5-dihydro-1H-phosphole 1-oxides

János Kovács, Nóra Balázsdi Szabó, Zoltán Nagy, K. Ludányi, G. Keglevich

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Novel 7-phosphanorbornene derivatives, such as 4, 5, 10, and 11 were synthesized utilizing 1-phenyl-2-methyl-2,5-dihydro-1H-phosphole oxide (1) and 1-cyclohexyl-3-methyl-2,5-dihydro-1H-phosphole oxide (7) as the starting materials. Products 4 and 10 were prepared by trapping the corresponding phosphole oxide intermediates (3 and 9, respectively) by N-phenylmaleimide, while 5 and 11 were obtained by the dimerization of 3 and 9, respectively. The trapping reaction was studied in details; on one hand, bromo-2,3-dihydro-1H- phosphole oxides (6-1 and 6-2) were pointed out as the intermediates, on the other hand, the trapping reaction was optimized. Bridged P-heterocycles 4, 5, 10, and 11 were tested in the fragmentation-related phosphorylation of methanol. Hydrogenation of phosphanorbornenes 4 and 5 led to the corresponding phosphanorbornanes (12 and 14, respectively) and to a reductive type of retro cycloaddition.

Original languageEnglish
Pages (from-to)320-326
Number of pages7
JournalHeteroatom Chemistry
Volume16
Issue number5
DOIs
Publication statusPublished - 2005

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Oxides
Phosphorylation
Cycloaddition
Dimerization
Hydrogenation
Methanol
Derivatives

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

New 7-phosphanorbornenes derived from 2-methyl-1-phenyl- And 1-cyclohexyl-3-methyl-2,5-dihydro-1H-phosphole 1-oxides. / Kovács, János; Szabó, Nóra Balázsdi; Nagy, Zoltán; Ludányi, K.; Keglevich, G.

In: Heteroatom Chemistry, Vol. 16, No. 5, 2005, p. 320-326.

Research output: Contribution to journalArticle

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