2,4,6-Tris(4-Iodophenyl)-1,3,5-trimethylbenzene
, Narcisa Laura Marangoci 1, Alexandru Rotaru 1, Alexandru Florentin Trandabat 2 and Lucian Gabriel Bahrin 1,*Round 1
Reviewer 1 Report
The herein shown synthesis of one compound may fit in the scope of the journal but some details are not yet clear. Most importantly the authors write that iodine is used in the experimental section but this is nowhere discussed or mentioned in the main text. This is absolutely unclear and given the fact that the PIFA is used in a stoichiometric amount this raises questions that have to be addressed. In addition I wonder how other aromatic iodination approaches work (that are maybe not using the hypervalente iodine reagent). So even if the main purpose of this paper in this journal is to provide a way for a new compound I think the authors should at least show a few additional iodination conditions to give the readers a bit of an idea why the chosen cond. were finally used (a paper should tell a story, although in this journal).
The NMR interpretation should be checked because at least according to the provided copy the aromatic signals appear as doublets not multiplets (which also makes sense). Please check and eventually correct this.
Author Response
Comment: Most importantly the authors write that iodine is used in the experimental section but this is nowhere discussed or mentioned in the main text. This is absolutely unclear and given the fact that the PIFA is used in a stoichiometric amount this raises questions that have to be addressed.
Answer: Thank you for the observation, we replaced ”PIFA in chloroform” on line 31 with “PIFA and iodine in chloroform”. Concerning the amounts used, we followed a procedure previously reported, which was cited accordingly (reference 16). As a consequence, “according to a procedure already established [16]” was added on line 31.
Comment: In addition I wonder how other aromatic iodination approaches work (that are maybe not using the hypervalente iodine reagent). So even if the main purpose of this paper in this journal is to provide a way for a new compound I think the authors should at least show a few additional iodination conditions to give the readers a bit of an idea why the chosen cond. were finally used (a paper should tell a story, although in this journal).
Answer: In order to improve the discussions on the iodination approaches, several other methods were briefly described in the revised version of the manuscript and three new references were added to the manuscript. The sentence “Unlike other iodination reactions, this particular system does not use strong acids, such as the sulfuric acid/nitric acid/iodine system [17], potentially explosive reagents, as found in the case of the sulfuric acid/iodine/periodic acid system [18] or toxic metals, such as mercury acetate [19].” was added on line 32.
Comment: The NMR interpretation should be checked because at least according to the provided copy the aromatic signals appear as doublets not multiplets (which also makes sense). Please check and eventually correct this.
Answer: Thank you for pointing this inconsistency out. We replaced “multiplet between 7.91-7.65 ppm” on line 44 with “doublet at 7.82, with a coupling constant 3J=7.8 Hz”. Also, replaced “multiplet between 7.08-6.84 ppm” on line 46 with “doublet at 6.97 ppm, with a coupling constant 3J=7.9 Hz”.
Round 2
Reviewer 1 Report
The comments were addressed properly. Only please update the first scheme as the iodine is missing there as well!
But this can be done in a minor revision and I do not request to review the manuscript any further.
Author Response
Again, thank you for taking the time to go through our manuscript. Scheme 1 was updated accordingly.
