Role of Steric Hindrance in the Newman-Kwart Rearrangement and in the Synthesis and Photophysical Properties of Arylsulfanyl Tetrapyrazinoporphyrazines

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F14%3A39898421" target="_blank" >RIV/00216275:25310/14:39898421 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11160/14:10282181 RIV/60162694:G44__/14:43875123
Result on the web
<a href="http://dx.doi.org/10.1021/jo402791c" target="_blank" >http://dx.doi.org/10.1021/jo402791c</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/jo402791c" target="_blank" >10.1021/jo402791c</a>

Result language
angličtina
Original language name
Role of Steric Hindrance in the Newman-Kwart Rearrangement and in the Synthesis and Photophysical Properties of Arylsulfanyl Tetrapyrazinoporphyrazines
Original language description
Conditions for the Newman-Kwart rearrangement of phenols into thiophenols were investigated in relation to the bulkiness of substituents at the 2 and 6 positions of the starting phenol derivative with an emphasis on eliminating side reactions. Thiophenols with different 2,6-disubstitution patterns (including hydrogen, methyl, isopropyl or tert-butyl groups) were used for the synthesis of 5,6-bis(arylsulfanyl)-pyrazine-2,3-dicarbonitriles that underwent cyclotetramerization leading to the corresponding zinc tetrapyrazinoporphyrazines (TPyzPz), aza-analogues of phthalocyanines. Several methods for the cyclotetramerization were attempted to eliminate problematic side reactions. Magnesium butoxide was found as the most suitable cyclotetramerization agent and afforded TPyzPzs in reasonable yields of approximately 30% under mild conditions. The varying arrangements of the peripheral substitutions resulting from the different bulkiness of the substituents were demonstrated by the X-ray struct
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CA - Inorganic chemistry
OECD FORD branch
—

Project
<a href="/en/project/GA13-27761S" target="_blank" >GA13-27761S: Development of new photosensitizers for photodynamic therapy and investigation of their mechanism of action on cellular level</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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