Details
| Original language | English |
|---|---|
| Pages (from-to) | 137-144 |
| Number of pages | 8 |
| Journal | Chemische Berichte |
| Volume | 127 |
| Issue number | 1 |
| Publication status | Published - Jan 1994 |
| Externally published | Yes |
Abstract
exo‐7‐Chloro‐endo‐7‐phenylbicyclo[3.2.0]hept‐2‐en‐6‐one (5) undergoes cine substitution reactions with methoxide anions and with dialkylamines to give 5‐methoxy or 5‐dialkylamino derivatives 13, 14, 16–19 in high yield. While attempts directed to an acetalization have failed, the addition of Grignard reagents to the methoxy derivatives proceeds stereoselectively in high yield. Hydrochlorides 20/21 lose amine at 110°C to form 2‐phenyltropone 22. Thermolysis of diethylamino derivative 24 at 170°C (temperature determined by DSC) results in the formation of the dienaminone 25.
Keywords
- Bicyclo[3.2.0]hept‐2‐en‐6‐one, cine substitution, DSC
ASJC Scopus subject areas
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Chemische Berichte, Vol. 127, No. 1, 01.1994, p. 137-144.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of 5‐Methoxy‐ and 5‐(Dialkylamino)bicyclo[3.2.0]hept‐2‐en‐6‐one Derivatives by cine Substitution with Methoxide Anions and Dialkylamines
AU - Butenschön, Holger
PY - 1994/1
Y1 - 1994/1
N2 - exo‐7‐Chloro‐endo‐7‐phenylbicyclo[3.2.0]hept‐2‐en‐6‐one (5) undergoes cine substitution reactions with methoxide anions and with dialkylamines to give 5‐methoxy or 5‐dialkylamino derivatives 13, 14, 16–19 in high yield. While attempts directed to an acetalization have failed, the addition of Grignard reagents to the methoxy derivatives proceeds stereoselectively in high yield. Hydrochlorides 20/21 lose amine at 110°C to form 2‐phenyltropone 22. Thermolysis of diethylamino derivative 24 at 170°C (temperature determined by DSC) results in the formation of the dienaminone 25.
AB - exo‐7‐Chloro‐endo‐7‐phenylbicyclo[3.2.0]hept‐2‐en‐6‐one (5) undergoes cine substitution reactions with methoxide anions and with dialkylamines to give 5‐methoxy or 5‐dialkylamino derivatives 13, 14, 16–19 in high yield. While attempts directed to an acetalization have failed, the addition of Grignard reagents to the methoxy derivatives proceeds stereoselectively in high yield. Hydrochlorides 20/21 lose amine at 110°C to form 2‐phenyltropone 22. Thermolysis of diethylamino derivative 24 at 170°C (temperature determined by DSC) results in the formation of the dienaminone 25.
KW - Bicyclo[3.2.0]hept‐2‐en‐6‐one, cine substitution
KW - DSC
UR - http://www.scopus.com/inward/record.url?scp=84989466103&partnerID=8YFLogxK
U2 - 10.1002/cber.19941270122
DO - 10.1002/cber.19941270122
M3 - Article
AN - SCOPUS:84989466103
VL - 127
SP - 137
EP - 144
JO - Chemische Berichte
JF - Chemische Berichte
SN - 0009-2940
IS - 1
ER -