Stereospezifische Synthese und Isomerisierung der 10‐Chlor‐decahydroisochinoline. Decahydroisochinoline. IV. Teil | Zendy

Grob C. A. | Zendy; Wohl R. A. | Zendy

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Stereospezifische Synthese und Isomerisierung der 10‐Chlor‐decahydroisochinoline. Decahydroisochinoline. IV. Teil

Author(s) -

Grob C. A.,

Wohl R. A.

Publication year - 1966

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19660490804

Subject(s) - chemistry , chloride , formaldehyde , medicinal chemistry , acetic acid , aqueous solution , hydrogen chloride , isomerization , ring (chemistry) , catalysis , stereochemistry , organic chemistry

Treatment of cis‐ and trans ‐10‐hydroxy‐N‐methyl‐decahydroisoquinoline, ( 3a ) and ( 10a ) respectively, or N‐methyl‐Δ 9,10 ‐octahydroisoquinoline ( 4 a ) with hydrogen chloride in acetic acid affords the thermodynamically more stable trans ‐isomer of 10‐chloro‐N‐methyl‐decahydroisoquinoline ( 1a ). On the other hand ring closure of β‐(cyclohexen‐1‐yl)‐ethylamines 11a or 11b with aqueous formaldehyde in the presence of chloride ions leads to the 10‐ cis ‐chlorides 2a or 2b in a kinetically controlled reactions.

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