A New Method for the Synthesis of 1-(1-Isocyanoethyl)adamantane
Round 1
Reviewer 1 Report
Comments and Suggestions for AuthorsPitushkin and coworkers reported a novel single-step method for the synthesis of 1-(1-isocyanoethyl)adamantane from 1-(1-adamantylethyl)amine. This method has as an advantage that no toxic reagents as POCl3 or triphosgene are needed. Besides, higher yields are obtained by this method than with previously reported.
This reviewer thinks that the article may be accepted for publication after minor revisions.
The authors did not mention whether they obtained a solid or an oil and neither the colour of the compound. They should specify it. Besides, if it is a solid, they should provide a melting point of the compound.
In the references there are twice the numbers for each reference. This should be corrected.
Author Response
Thank you very much for taking the time to review this manuscript.
Reviewer:
Pitushkin and coworkers reported a novel single-step method for the synthesis of 1-(1-isocyanoethyl)adamantane from 1-(1-adamantylethyl)amine. This method has as an advantage that no toxic reagents as POCl3 or triphosgene are needed. Besides, higher yields are obtained by this method than with previously reported.
This reviewer thinks that the article may be accepted for publication after minor revisions.
The authors did not mention whether they obtained a solid or an oil and neither the colour of the compound. They should specify it. Besides, if it is a solid, they should provide a melting point of the compound.
Response:
The resulting isonitrile is a light yellow liquid.
Reviewer:
In the references there are twice the numbers for each reference. This should be corrected.
Response:
Сorrected.
Reviewer 2 Report
Comments and Suggestions for AuthorsDmitry Pitushkin and his coworkers have reported “A new method for the synthesis of 1-(1-isocyanoethyl)adamantane.” They have developed a method to synthesize 1-(1-isocyanoethyl)adamantane by optimizing various bases using chloroform as a reagent and dichloromethane and t-BuOH as solvents at 20-40 oC temperature. In this way, they improved the yield from 0-92%. I feel this manuscript can be published in its present form.
They achieved an excellent yield in the synthesis of 1-(1-isocyanoethyl)adamantane by using t-BuOK as a base.
The literature on synthesizing isocyanides under mild conditions is quite limited, which prompted me to recognize its relevance to the field.
The published data typically involve somewhat harsh conditions for synthesizing isocyanides. However, this manuscript demonstrates the use of mild conditions, simplifying the chemist's work.
The author should improve the reaction conditions by using readily available reagents, milder conditions, reducing costs, and increasing the yield and etc.
Their primary objective was to improve the conditions for synthesizing adamantane isocyanides. They discovered a mild method that yields the desired compound in higher amounts compared to previously reported methods.
References are appropriate. But they numbered two times for each reference. They should correct it before publication.
In Figure 1, the name of the second structure is incorrect. The authors should correct this before publication.
In the conclusion, the authors stated that this method is applicable for preparing other isocyanides. To enhance the quality of the data, the authors should test 4-5 additional amines for isocyanide synthesis and include the results in the manuscript.
Minor editing of English language required
Author Response
Thank you very much for taking the time to review this manuscript.
Reviewer:
Dmitry Pitushkin and his coworkers have reported “A new method for the synthesis of 1-(1-isocyanoethyl)adamantane.” They have developed a method to synthesize 1-(1-isocyanoethyl)adamantane by optimizing various bases using chloroform as a reagent and dichloromethane and t-BuOH as solvents at 20-40 oC temperature. In this way, they improved the yield from 0-92%. I feel this manuscript can be published in its present form.
They achieved an excellent yield in the synthesis of 1-(1-isocyanoethyl)adamantane by using t-BuOK as a base.
The literature on synthesizing isocyanides under mild conditions is quite limited, which prompted me to recognize its relevance to the field.
The published data typically involve somewhat harsh conditions for synthesizing isocyanides. However, this manuscript demonstrates the use of mild conditions, simplifying the chemist's work.
The author should improve the reaction conditions by using readily available reagents, milder conditions, reducing costs, and increasing the yield and etc.
Their primary objective was to improve the conditions for synthesizing adamantane isocyanides. They discovered a mild method that yields the desired compound in higher amounts compared to previously reported methods.
References are appropriate. But they numbered two times for each reference. They should correct it before publication.
Response:
Сorrected.
Reviewer:
In Figure 1, the name of the second structure is incorrect. The authors should correct this before publication.
Response:
Сorrected.
Reviewer:
In the conclusion, the authors stated that this method is applicable for preparing other isocyanides. To enhance the quality of the data, the authors should test 4-5 additional amines for isocyanide synthesis and include the results in the manuscript.
Response:
Work on obtaining new isonitriles is currently ongoing. Using the developed method, 2 aromatic isonitriles were obtained: 1-fluoro-3-isocyanobenzene and 1-chloro-3-isocyanobenzene, and therefore we conclude that the method is universal. However, this work is not yet completed and requires some time to complete. Therefore, we cannot publish these data until we complete a series of reactions involving amines with various substituents (aliphatic, alicyclic, aromatic and heteroaromatic).
In addition, the format of the submitted material (one compound is enough) in this case will be significantly expanded (description of methods, presentation of spectra, etc.) and it may not meet the requirements for publications. Please correct the conclusion in the form “...may be applicable”
