[(N-benzamidomethyl)(N-benzoyl)amino]methyltriphenylphosphonium Tetrafluoroborate

Round 1

Reviewer 1 Report

This focussed and concise paper contained an account of the development of the selective synthesis of an unexpected salt which appears to be unusual and novel in structure. 

Following an unexpected observation on an attempted Wittig reaction, the researchers isolated a novel salt formed by the reaction between two equivalents of the substrate, presumably through elimination of a PPh3 from one equivalent followed by trapping of the (assumed) iminium cation or imine intermediate by the second equivalent. The reaction was carefully optimised through variation of solvent and conditions to give a product in up to 73% yield as the single product.

It is a very interesting transformation, and the product was isolated in good yield and characterised in detail. The 1H NMR revealed it to be clean and matched the proposed structure, as did the mass spectrometry. The work was carried out to a high standard, with a full procedure provided, along with detailed characterisation data.

for section 3.3m I would also include a procedure without the benzaldehyde, since this is not required for the reaction.

The paper is well-written and easy to follow- the result is well communicated, and the supporting information is valuable. The references serve to place the results into appropriate context.

I am happy to recommend the publication of this paper, pending the slight change to the experimental section above. I could detect no significant minor typographical errors. 

The authors might also want to check the spelling of 'N-1-(benzotriazolil)alkylamides' in the introduction as I was not familiar with this term. is it '...triazolyl...'?

Well written with no significant typographical errors.

Author Response

Thank you very much for your review and warm reception of the article. We are convinced that your comments and suggestions significantly improved the scientific value of our paper.

1. ‘for section 3.3m I would also include a procedure without the benzaldehyde, since this is not required for the reaction’
   • we have rearranged section 3 a little, we have described the procedure with the use of benzaldehyde (3.2) and added the procedure without the use of benzaldehyde (3.3)
2. ‘The authors might also want to check the spelling of 'N-1-(benzotriazolil)alkylamides' in the introduction as I was not familiar with this term. is it '...triazolyl...'?’
   • the Reviewer is absolutely right - we have corrected the translation of the chemical name

Yours sincerely,

Jakub Adamek