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Unequivocal Experimental Evidence for a Unified Lithium Salt-Free Wittig Reaction Mechanism for All Phosphonium Ylide Types: Reactions with β-Heteroatom-Substituted Aldehydes Are Consistently…

Overview of attention for article published in Journal of the American Chemical Society, May 2012
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Title
Unequivocal Experimental Evidence for a Unified Lithium Salt-Free Wittig Reaction Mechanism for All Phosphonium Ylide Types: Reactions with β-Heteroatom-Substituted Aldehydes Are Consistently Selective forcis-Oxaphosphetane-Derived Products
Published in
Journal of the American Chemical Society, May 2012
DOI 10.1021/ja300943z
Pubmed ID
Authors

Peter A. Byrne, Declan G. Gilheany

Abstract

The true course of the lithium salt-free Wittig reaction has long been a contentious issue in organic chemistry. Herein we report an experimental effect that is common to the Wittig reactions of all of the three major phosphonium ylide classes (non-stabilized, semi-stabilized, and stabilized): there is consistently increased selectivity for cis-oxaphosphetane and its derived products (Z-alkene and erythro-β-hydroxyphosphonium salt) in reactions involving aldehydes bearing heteroatom substituents in the β-position. The effect operates with both benzaldehydes and aliphatic aldehydes and is shown not to operate in the absence of the heteroatom substituent on the aldehyde. The discovery of an effect that is common to reactions of all ylide types strongly argues for the operation of a common mechanism in all Li salt-free Wittig reactions. In addition, the results are shown to be most easily explained by the [2+2] cycloaddition mechanism proposed by Vedejs and co-workers as supplemented by Aggarwal, Harvey, and co-workers, thus providing strong confirmatory evidence in support of that mechanism. Notably, a cooperative effect of ortho-substituents in the case of semi-stabilized ylides is confirmed and is accommodated by the cycloaddition mechanism. The effect is also shown to operate in reactions of triphenylphosphine-derived ylides and has previously been observed for reactions under aqueous conditions, thus for the first time providing evidence that kinetic control is in operation in both of these cases.

Twitter Demographics

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Mendeley readers

The data shown below were compiled from readership statistics for 94 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Netherlands 1 1%
Czechia 1 1%
Italy 1 1%
Unknown 91 97%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 30 32%
Student > Bachelor 17 18%
Student > Master 15 16%
Researcher 14 15%
Student > Postgraduate 3 3%
Other 8 9%
Unknown 7 7%
Readers by discipline Count As %
Chemistry 80 85%
Agricultural and Biological Sciences 3 3%
Biochemistry, Genetics and Molecular Biology 2 2%
Nursing and Health Professions 1 1%
Engineering 1 1%
Other 0 0%
Unknown 7 7%

Attention Score in Context

This research output has an Altmetric Attention Score of 2. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 09 February 2021.
All research outputs
#11,302,114
of 18,593,253 outputs
Outputs from Journal of the American Chemical Society
#48,171
of 56,197 outputs
Outputs of similar age
#75,998
of 136,710 outputs
Outputs of similar age from Journal of the American Chemical Society
#359
of 518 outputs
Altmetric has tracked 18,593,253 research outputs across all sources so far. This one is in the 37th percentile – i.e., 37% of other outputs scored the same or lower than it.
So far Altmetric has tracked 56,197 research outputs from this source. They typically receive a little more attention than average, with a mean Attention Score of 6.2. This one is in the 13th percentile – i.e., 13% of its peers scored the same or lower than it.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 136,710 tracked outputs that were published within six weeks on either side of this one in any source. This one is in the 42nd percentile – i.e., 42% of its contemporaries scored the same or lower than it.
We're also able to compare this research output to 518 others from the same source and published within six weeks on either side of this one. This one is in the 30th percentile – i.e., 30% of its contemporaries scored the same or lower than it.