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Stereospezifische Umwandlungen des (+)‐2‐ und (+)‐3‐Carens in optisch aktive Siebenring‐Systeme
Author(s) -
Eilbracht Peter,
Winkels Irmgard
Publication year - 1991
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.19911240128
Subject(s) - chemistry , isomerization , cycloheptane , ring (chemistry) , bicyclic molecule , stereospecificity , stereochemistry , optically active , double bond , medicinal chemistry , organic chemistry , catalysis
Stereospecific Conversions of (+)‐2‐ and (+)‐3‐Carene into Optically Active Seven‐Membered Ring Systems The reactions of (+)‐2‐carene ( 6b ) and (+)‐3‐carene ( 15 ) with iron carbonyls are studied under various conditions. Besides double bond isomerization and interconversion of the two isomeric hydrocarbons, at least two different modes of ring opening leading to six‐ and seven‐membered ring products are observed. Under mild conditions the primary ring opening complex 7b is isolated without loss of sterical information. Carbonylation of 7b under various conditions yields optically active cycloheptane systems 18, 19 , and 20 or the bicyclic systems 9b and 10b .