A new use of wittig-type reagents as 1,3-dipolar cycloaddition precursors and in pyrrole synthesis

Journal of the American Chemical Society

Volumn 129, Issue 41, 2007, Pages 12366-12367

  St Cyr, Daniel J ^a   Arndtsen, Bruce A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; PHOSPHORUS DERIVATIVE; PYRROLE DERIVATIVE; REAGENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; WITTIG REACTION;

EID: 35348985374     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074330w     Document Type: Article

References (30)

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11. 5 In addition, for the closest related example, a trifluoromethyl-substituted [1,4,2]-oxazaphospholine has been shown to behave as a dipole precursor (Burger, K.; Fehn, J.; Moll, E. Chem. Ber. 1971, 104, 1826). However, a simple phosphorus ylide (e.g., 2′) has not been used as a 1,3-dipole.
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29. In contrast, the palladium-catalyzed pyrrole synthesis from these reagents is limited to stabilized imines and acid chlorides (ref 4a).
30. A 2:1 mixture of these pyrroles is generated via Münchnones.