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Reaktion von 2,2‐Dichlor‐1‐methyl‐3‐phenylcyclopropanmethanol‐tetrahydropyranylether mit Butyllithium/CO 2 und Folgereaktionen der Produkte
Author(s) -
Hülskämper Ludwig,
Weyerstahl Peter
Publication year - 1984
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19841171218
Subject(s) - chemistry , yield (engineering) , medicinal chemistry , cyclopropene , hydrolysis , butyllithium , ether , hydroxymethyl , organic chemistry , materials science , metallurgy
Reaction of 2,2‐Dichloro‐1‐methyl‐3‐phenylcylopropanemethanol Tetrahydropyranyl Ether with Butylliuthium/CO 2 and Subsequent Reactions of the Products While the title reaction starting from 2a followed by acidic work‐up affords only the α‐chlorolactone 1 with low yield, alcaline work‐up and addition of dimethyl sulfate lead to a mixture of the esters 2b and c and the chlorocyclopropene 3a. From 2b/c with KO t Bu the cyclopropene ester 3f is formed. Hydrolysis of 3a (↠3d), 3f (↠3g) , and 2b (↠2d) gives the hydroxymethyl compounds, while 2c is lactonized directly to 1 .