Document Detail


Reaction of Resorcinol with alpha,beta-Unsaturated Ketones.
MedLine Citation:
PMID:  11672054     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Products of the acid-catalyzed reaction of resorcinol with alpha,beta-unsaturated ketones have been found to fall into two classes. The first type of product is illustrated by 4-(3,4-dihydro-7-hydroxy-2,4,4-trimethyl-2H-1-benzopyran-2-yl)-1,3-benzenediol, 1, formed in 91% yield by the reaction of resorcinol with 4-methyl-3-penten-2-one (mesityl oxide). The second type of product is illustrated by (C(2)-symmetric) 2,2'-spirobi(7-hydroxy-4,4-dimethylchroman),4, formed in 85% yield by the reaction of resorcinol with 2,6-dimethyl-2,5-heptadien-4-one (phorone). A number of examples of reactions leading, in quite good yields, to products analogous to 1are presented, as well as some reactions that fail. Flavan 1 is identical to the compound formed by the acid-catalyzed reaction of acetone with excess resorcinol. Compound 1 and a steroidal analogue of 1 have been found to be fluorescent.
Authors:
P. Livant; Weizheng Xu
Related Documents :
20976324 - Tandem [4 + 1 + 1] annulation and metal-free aerobic oxidative aromatization: straightf...
18931774 - Rhodium-catalysed hydroacylation or reductive aldol reactions: a ligand dependent switc...
12816424 - 1-bromo-1-lithioethene: a practical reagent for the efficient preparation of 2-bromo-1-...
11895394 - [3 + 2] annulation of beta-heteroatom-substituted alpha,beta-unsaturated acylsilanes wi...
22612264 - Catalytic asymmetric synthesis of secondary nitriles via stereoconvergent negishi aryla...
15186144 - Isotope effects in photochemistry. 1. o-nitrobenzyl alcohol derivatives.
Publication Detail:
Type:  JOURNAL ARTICLE    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  63     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  1998 Feb 
Date Detail:
Created Date:  2001-Oct-23     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  636-641     Citation Subset:  -    
Affiliation:
Department of Chemistry, Auburn University, Auburn, Alabama 36849-5312.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Radical Ion Probes. 9. The Chemistry of Radical Cations Derived from 9-Cyclopropylanthracene and 9-B...
Next Document:  Stereoselective Synthesis of a Key Precursor of Halicholactone and Neohalicholactone.