N-(p-Toluenesulfonyl)-1-(4′-acetylphenoxy)acrylimidate: Synthesis, Crystal Structure and Theoretical Studies
, Alberto Cedillo-Cruz 1,2, Raúl Eduardo Gordillo-Cruz 1,2, Diego Martínez-Otero 1,3, M. V. Basavanag Unnamatla 1,2 and Erick Cuevas-Yañez 1,2,*
Round 1
Reviewer 1 Report
This manuscript is one of a series of studies in which the authors have reported using different alkyne and azide derivatives in alkyne-azide-cyclization. Although the compounds in this manuscript are sufficient, there is only one example of the reaction. The reaction mechanism is only analogous, which is insufficient for a paper and gives the impression that the article is divided into separate reports.
Therefore, the paper should be published after adding several examples using alkyne derivatives or compounds with different azide substituents.
Author Response
According to Journal´s scope, manuscripts comprise one-compound-per-paper short notes on synthetic compounds and natural products. Although it is true that the reviewer has rightly pointed out the necessity of more examples, these are not mandatory for the purposes of this report; therefore, they are going to be performed for future works, we appreciate the suggestions.
Reviewer 2 Report
The manuscript "N-(p-toluenesulfonyl)-1-(4’-Acetylphenoxy)acrylimidate: Synthesis, Crystal Structure and Theoretical Studies" by Escandón-Mancilla et al. describes the synthesis of the title compound as a result of an attempted triazole formation. The authors provide ample proof for the structure of the unexpected product (FTIR, 1H and 13C NMR, X-ray structure) and show quantum chemical evaluations in additon.
The NMR data and the CIF report are provided in the SI, seem to be in order and verify the structure proposed by the authors. The chosen level of theory (PBE1PBE/cc-pVDZ) is appropriate for this problem.
The proposed mechanism looks unusual at first, but Refs. [1], [2], [8], [9] and [10] confirm its plausibility.
Therefore, this reviewer recommends this paper for publication. It would have been interesting to test the substrate scope of this rearrangement with regards to:
1) The aryloxy residue
2) The substitution of the carbon adjacent to the aryloxy group in the propyne group
to demonstrate its versatility in synthesis, but perhaps the authors will do this in a follow-up publication.
It would also be interesting to test when the reaction stops at the triazole stage and when it proceeds to open the ring, but this is a topic for another paper.
Notes:
1) I highly recommend the authors provide the SI document as a pdf, not a docx file. Different users use different text editing software, which may not represent the contents of the file accurately (e.g. Microsoft Word vs. OpenOffice, LibreOffice).
2) Does the SI file contain a picture of the FTIR spectra? It does not show up in my file. If it is missing, please add it.
Author Response
These are great suggestions that we will further pursue, thank you very much for bring these to our attention.
Round 2
Reviewer 1 Report
As the author suggested, the paper would be suitable for the paper.
