Synthesis of Benzobis[1,3]oxathiins | Zendy

Mayer Axel | Zendy; Rumpf Norbert | Zendy; Hillmann Sabine | Zendy; Meier Herbert | Zendy

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Synthesis of Benzobis[1,3]oxathiins

Author(s) -

Mayer Axel,

Rumpf Norbert,

Hillmann Sabine,

Meier Herbert

Publication year - 2015

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.201500083

Subject(s) - chemistry , acetone , valence (chemistry) , stereochemistry , medicinal chemistry , computational chemistry , organic chemistry

Two different synthetic concepts led to the formation of 17, 19 , and 29 , the first structural isomeric benzobis[1,3]oxathiins. Hetero‐ DielsAlder reactions of diethyl mesoxylate 14 and the open valence isomers of the benzobisthietes 12 and 18 yielded the linear benzobis[1,3]oxathiin 17 and its angular isomer 22 , respectively. The isomeric angular system 29 could be obtained by a twofold O , S ‐acetalization reaction of the dihydroxydisulfanyl compound 27 and acetone ( 28 ).

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