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Process Safety Assessment of the Iron-Catalyzed Direct Olefin Diazidation for the Expedient Synthesis of Vicinal Primary Diamines.

ABSTRACT: We report herein a process safety assessment of the iron-catalyzed direct olefin diazidation for the preparation of a broad range of synthetically valuable vicinal primary diamines. Differential scanning calorimetry analysis of the corresponding reagents, intermediates, and a list of representative diazide/diaminium salt products revealed that all of them are thermal stable at the reaction temperature. The drop weight test of the diazides suggested that they are moderately impact-sensitive. Guided by this assessment, an optimized olefin diazidation/diamination procedure has been developed which allows for the gram-scale diaminium salt synthesis without purification of the diazide intermediate.

SUBMITTER: Zhu HT

PROVIDER: S-EPMC5773106 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Process Safety Assessment of the Iron-Catalyzed Direct Olefin Diazidation for the Expedient Synthesis of Vicinal Primary Diamines.

Zhu Hai-Tao HT Arosio Luca L Villa Roberto R Nebuloni Marino M Xu Hao H

Organic process research & development 20171108 12

We report herein a process safety assessment of the iron-catalyzed direct olefin diazidation for the preparation of a broad range of synthetically valuable vicinal primary diamines. Differential scanning calorimetry analysis of the corresponding reagents, intermediates, and a list of representative diazide/diaminium salt products revealed that all of them are thermal stable at the reaction temperature. The drop weight test of the diazides suggested that they are moderately impact-sensitive. Guid ...[more]

PMID: 29353989

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