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A direct retro-Reformatsky fragmentation: formal ring enlargement of cyclic ketones for novel and practical synthesis of heterocyclic enamines.

Abstract:

A novel and practical synthesis of heterocyclic enamines has been developed from the formal ring enlargement of cyclic ketones, which comprised the retro-Reformatsky fragmentation reaction as a key step. Under alkaline bromination conditions, the Reformatsky adducts derived from five- to seven-membered cyclic ketones underwent efficiently a direct retro-Reformatsky fragmentation, followed by spontaneous alpha,alpha-dibromination, to produce alpha,alpha,omega-tribromo-beta-ketoester compounds ...

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Publication status:
Published

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Publisher copy:
10.1021/jo0351320

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Journal:
The Journal of organic chemistry
Volume:
69
Issue:
3
Pages:
997-1000
Publication date:
2004-02-05
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:76f84b6f-1fd9-4239-a9fe-f9400501e634
Source identifiers:
38930
Local pid:
pubs:38930
Language:
English

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