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Keywords = Herz reaction

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8 pages, 1493 KiB  
Short Note
6-Chloro-3H-benzo[d][1,2,3]dithiazol-2-ium Chloride
by Alexander J. Nicholls and Ian R. Baxendale
Molbank 2022, 2022(1), M1339; https://doi.org/10.3390/M1339 - 11 Feb 2022
Cited by 1 | Viewed by 2461
Abstract
This short note describes the synthesis of an amorphous benzo[1,2,3]dithiazole chloride salt (commonly known as a ‘Herz salt’) by use of the Herz reaction. Hetero- and homolytic transformations of this species to a variety of useful adducts in medicinal and materials chemistry are [...] Read more.
This short note describes the synthesis of an amorphous benzo[1,2,3]dithiazole chloride salt (commonly known as a ‘Herz salt’) by use of the Herz reaction. Hetero- and homolytic transformations of this species to a variety of useful adducts in medicinal and materials chemistry are well established, although there are limited examples of isolation in the literature, and characterisation data is even harder find. While several studies have confirmed the structure of the benzodithiazole ring beyond doubt, (having generated suitably crystalline salts with large counterions for XRD-analysis), there remains value in understanding and optimising the synthesis of the simple, amorphous polymorphs. For the first time, MS data is provided for this compound and a new mechanism of its formation is proposed based upon new experimental observations and data. Full article
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34 pages, 13479 KiB  
Review
Benzo[1,2,3]dithiazole Compounds: A History of Synthesis and Their Renewed Applicability in Materials and Synthetic Chemistry, Originating from the Herz Reaction
by Alexander J. Nicholls and Ian R. Baxendale
Reactions 2021, 2(3), 175-208; https://doi.org/10.3390/reactions2030013 - 29 Jun 2021
Cited by 8 | Viewed by 6135
Abstract
The benzo[1,2,3]dithiazole is a unique heteroaromatic functionality whose conjugated profile instils some fascinating electronic properties. This has been historically recognized in the design and manufacture of organic dyes early last century. Although, with the benefit of increased diagnostic techniques and improved understanding, these [...] Read more.
The benzo[1,2,3]dithiazole is a unique heteroaromatic functionality whose conjugated profile instils some fascinating electronic properties. This has been historically recognized in the design and manufacture of organic dyes early last century. Although, with the benefit of increased diagnostic techniques and improved understanding, these structures are attracting greater attention in additional research settings, including applications as organic radicals and semiconductors. In addition, the benzodithiazole functionality has been shown to be a valuable synthetic intermediate in the preparation of a variety of other privileged aromatic and heteroaromatic targets, many of which are important APIs. In this review, the authors aim to critically analyse the potential applicability of these compounds to the fields of not only small-scale laboratory synthetic and medicinal chemistry but also commercial-scale processes and increasingly materials chemistry. Full article
(This article belongs to the Special Issue Feature Papers in Reactions in 2021)
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