NDLI: Electron-rich heteroaroylphosphonates and their reaction with trimethyl phosphite

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Organic & Biomolecular Chemistry Vol -5

Organic & Biomolecular Chemistry Vol -4

Organic & Biomolecular Chemistry Vol -3

Organic & Biomolecular Chemistry Vol -2

Electron-rich heteroaroylphosphonates and their reaction with trimethyl phosphite

Content Provider	Royal Society of Chemistry (RSC)
Author	Harris, Jayne E. Duncanson, Philip Cheong, Yuen-Ki Salt, Michael C. Al-Jeboori, Mohamad J. Taylor, Helen V. Griffiths, D. Vaughan
Copyright Year	2008
Abstract	Dialkyl heteroaroylphosphonates based on thiophene, pyrrole or furan have been prepared and their reactions with trimethyl phosphite investigated. Deoxygenation of the carbonyl groups in these heteroaroylphosphonates occurs to give carbene intermediates, which then undergo further reaction. In the case of the furan-3-oylphosphonates and those systems containing a thiophene or pyrrole ring, the major reaction pathway involves intermolecular trapping of the carbene intermediates by the trimethyl phosphite, leading to the formation of ylidic phosphonates that can be readily converted into the corresponding 1,1-bisphosphonates. However, in some furan-2-oylphosphonates the carbenes generated undergo ring-opening to initially give acyclic alkynylphosphonates which may react further to give other novel phosphorus compounds. The effects of substituents on the extent to which intermolecular trapping of the initially formed carbene competes with intramolecular rearrangement has been investigated. The latter process appears to be suppressed by a substituent at the 5-position of the furan ring, the resulting ylidic phosphonates being a rare example of an efficient intermolecular trapping of a furan-2-yl carbene.
Starting Page	577
Ending Page	585
Page Count	9
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	6
Issue Number	3
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b717130g
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Furan Carbene Pyrrole Trimethyl phosphite Phosphorus Thiophene Carbonyl group Substituent Ylide
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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