The preparation and stereochemistry of 1‐chloroethyl‐4‐methyl‐6,7‐dimethoxyisochroman | Zendy

Mccall John M. | Zendy; Tenbrink Ruth E. | Zendy; Kamdar Bharat V. | Zendy; Chidester Constance | Zendy

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The preparation and stereochemistry of 1‐chloroethyl‐4‐methyl‐6,7‐dimethoxyisochroman

Author(s) -

Mccall John M.,

Tenbrink Ruth E.,

Kamdar Bharat V.,

Chidester Constance

Publication year - 1979

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570160232

Subject(s) - chemistry , boron trifluoride , acetal , catalysis , ethanol , boron , organic chemistry , medicinal chemistry , stereochemistry

The boron trifluoride catalyzed reaction of 2‐methyl‐2‐(3,4‐dimethoxypbenyl)ethanol and chloropropionaldehyde diethyl acetal yields a mixture of cis and trans 1‐ehloroethyl‐4‐methyl‐6,7‐dimethoxyisochroman. The structure of the trans compound was established by X‐ray analysis. The trans compound equilibrates to a mixture of the cis and trans when exposed to boron trifluoride catalyst.

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