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Synthesis of 3,7‐Disubstituted 9‐Thiatricyclo[3.3.1.0 3,7 ]nonane‐1,5‐dithiol Derivatives and Crystal Structure of Tetramethyl 3(4a H )‐Oxo‐1,4‐dihydrophenanthro[9,10‐ a ]pentalene‐1,2,4,4a‐tetracarboxylate
Author(s) -
Dölling Wolfgang,
Vogt Almut,
Baumeister Ute,
Hartung Helmut
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199811)1998:11<2647::aid-ejoc2647>3.0.co;2-v
Subject(s) - pentalene , chemistry , nonane , reagent , dithiol , octane , ring (chemistry) , bicyclic molecule , crystal structure , medicinal chemistry , organic chemistry , molecule
A simple and efficient approach to the 9‐thiatricyclo[3.3.1.0 3,7 ]nonane ring system ( 5 ) has been found by treating cis ‐bicyclo[3.3.0]octane‐3,7‐diones ( 1 ) with Lawesson's reagent or phosphorus pentasulfide. When dione 1 is treated with Lawesson's reagent tetramethyl 3(4a H )oxo‐1,4‐dihydrophenanthro[9,10‐ a ]pentalene‐1,2,4,4a‐tetracarboxylate ( 6 ) is obtained as a by‐product as shown by X‐ray structural analysis.