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A General Synthesis of ( Z )‐1,2‐Ethenediol Derivatives
Author(s) -
Wulff Günter,
Birnbrich Paul
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250227
Subject(s) - chemistry , yield (engineering) , ring (chemistry) , diol , stereochemistry , medicinal chemistry , diene , double bond , atom (system on chip) , organic chemistry , materials science , natural rubber , computer science , metallurgy , embedded system
By retro‐Diels‐Alder reaction of suitably substituted 9,10‐dihydro‐9,10‐ethanoanthracene‐ cis ‐11,12‐diol derivatives ( 4, 6, 8, 10, 12, 14 ) a number of known and unknown (Z)‐1,2‐disubstituted ethenes ( 5, 7, 9, 11, 13, 14 ) have been prepared in high yield, including derivatives with two different substituents. In contrast to this, attempts to prepare 1,3,2‐dioxasiloles bearing only substituents on the silicon atom gave dimers containing the ten‐membered ring system (Z,Z)2,2,7,7‐tetraalkyl‐1,3,6,8‐tetraoxa‐2,7‐disilacyclodeca‐4,9‐diene ( 19b, 21b, 23b, 25b ). Again these compounds are formed diastereoselectively with respect to the double bonds.