2012
DOI: 10.1002/anie.201202153
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Cascade Reactions Forming Highly Substituted, Conjugated Phospholes and 1,2‐Oxaphospholes

Abstract: More than just a carbon copy: The reaction of a phospha-Wittig-Horner reagent with diacetylenic ketones (see scheme) results in a cascade of reactions that can lead to both an oxaphosphole-terminated cumulene system and an alkene-bridged bis-phosphole. The reaction outcome is determined by the nature of the acetylene termini, with phenyl groups stabilizing a carbene intermediate that dimerizes to give the bis-phosphole product.

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Cited by 19 publications
(26 citation statements)
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“…The DFS and OS are different in the partial response category from the no response category in the outcome analysis. [61][62][63] Sataloff Classification for NAC Evaluation…”
Section: Chevallier System For Nac Evaluationmentioning
confidence: 99%
“…The DFS and OS are different in the partial response category from the no response category in the outcome analysis. [61][62][63] Sataloff Classification for NAC Evaluation…”
Section: Chevallier System For Nac Evaluationmentioning
confidence: 99%
“…Final proof for the structure of 2 was obtained by X‐ray diffraction analysis of single crystals of 2 a , obtained by slow evaporation of concentrated CH 2 Cl 2 solution. Comparing the crystal structure of 2 a with that reported earlier for 1 a 8a reveals some striking differences in the three‐dimensional structure of the compounds. Upon oxidation, the bond between C5 and C6 (Figure 1) decreases in order from a double bond with a normal bond length of 1.362 Å to a relatively long C sp2 C sp2 single bond (1.505(8) Å) in 2 a .…”
Section: Methodsmentioning
confidence: 61%
“…The very mild and reversible reduction (ca. −1.35 V vs. Fc 0/1+ ) supports the stabilization of the LUMO levels; however, no emission has been noted in this class of compounds …”
Section: Cyclic Structures Containing Phosphorus and Other Heteroelemmentioning
confidence: 67%
“…À1.35 Vv s. Fc 0/1 + ) supports the stabilization of the LUMO levels;h owever,n o emission has been noted in this class of compounds. [26,85]…”
Section: Benzoxabenzaza- and Benzthiaphospholesmentioning
confidence: 99%
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