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Aryl, hetaryl, and ferrocenyl thioketones as versatile building blocks for exploration in the organic chemistry of sulfur


Mloston, Grzegorz; Grzelak, Paulina; Hamera-Faldyga, Roza; Jasinski, Marcin; Pipiak, Paulina; Urbaniak, Katarzyna; Albrecht, Lukasz; Hejmanowska, Joanna; Heimgartner, Heinz (2017). Aryl, hetaryl, and ferrocenyl thioketones as versatile building blocks for exploration in the organic chemistry of sulfur. Phosphorus, Sulfur, and Silicon and the Related Elements, 192(2):204-211.

Abstract

Methods for the synthesis of hetaryl and ferrocenyl thioketones as well as applications of this class of organic sulfur compounds in the synthesis of both sulfur-containing and sulfur-free organic products are summarized. The most important applications relate to [2+2]-, [3+2]-, and [4+2]-cycloadditions. Aromatic thioketones react with diazomethane at −70°C, and the formed 1,3,4-thiadiazolines can be used as convenient precursors of reactive thiocarbonyl S-methanides. In contrast, the hetaryl thioketones do not form this type of cycloadducts. Reactions of hetaryl thioketones with thiocarbonyl S-methanides are proposed to occur via a stepwise diradical mechanism. Aryl and hetaryl thioketones react as prone heterodienophiles with cyclic and acyclic dienes. The first asymmetric synthesis of dihydrothiopyranes from aryl and hetaryl thioketones was performed using a L-proline-derived organocatalyst. Hetaryl thiochalcones are useful heterodienes for the preparation of hetaryl-substituted dihydrothiopyrans.

Abstract

Methods for the synthesis of hetaryl and ferrocenyl thioketones as well as applications of this class of organic sulfur compounds in the synthesis of both sulfur-containing and sulfur-free organic products are summarized. The most important applications relate to [2+2]-, [3+2]-, and [4+2]-cycloadditions. Aromatic thioketones react with diazomethane at −70°C, and the formed 1,3,4-thiadiazolines can be used as convenient precursors of reactive thiocarbonyl S-methanides. In contrast, the hetaryl thioketones do not form this type of cycloadducts. Reactions of hetaryl thioketones with thiocarbonyl S-methanides are proposed to occur via a stepwise diradical mechanism. Aryl and hetaryl thioketones react as prone heterodienophiles with cyclic and acyclic dienes. The first asymmetric synthesis of dihydrothiopyranes from aryl and hetaryl thioketones was performed using a L-proline-derived organocatalyst. Hetaryl thiochalcones are useful heterodienes for the preparation of hetaryl-substituted dihydrothiopyrans.

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Additional indexing

Item Type:Journal Article, refereed, further contribution
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:January 2017
Deposited On:13 Jan 2017 14:25
Last Modified:21 Nov 2017 18:53
Publisher:Taylor & Francis
ISSN:1042-6507
Funders:National Science Center (Cracow, Poland), Grant Maestro-3 (Dec-2012/06/A/ST5/00219, Ministry of Science and Higher Education, Poland, Iuventus Plus program (0008/IP3/2015/73)
Additional Information:Issue 2: 27th International Symposium on Organic Chemistry of Sulfur (ISOCS-27)
Publisher DOI:https://doi.org/10.1080/10426507.2016.1252368

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