ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The multiple isomerisation of 10α-bromo-N-methyl-decahydroisoquinoline (2a) is described. This compound is formed from 10β-hydroxy-N-methyl-decahydroisoquino-line (3a) and from N-methyl-Δ9,10- and -Δ5,10-octahydroisoquinoline, 4a and 5a respectively, in kinetically controlled reactions with HBr in acetic acid at 50°. At 85° the 10α-bromide 2a is converted via the axial 5β-trans-bromide 8a into the equatorial 5α-epimer 9a. At 140° an equilibrium mixture of 6β-, 6α-, and 7α-trans-bromides, 17a, 16a and 21a respectively, is obtained.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19650480723
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