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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
Abstract 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 ).