Stereochemistry and kinetics of amines addition to acetylenic esters
Keyword(s):
H Nmr
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The reactions of a series of methyl para-substituted phenylpropiolates 1a–e with piperidine, morpholine, and diethylamine in methanol and dimethylformamide (DMF) have been studied and their rates measured. The products were methyl β-(N,N-dialkylamino)-p-substituted cinnamates 2–4a–e. 1H NMR spectra were used to determine the configuration of the products. The ρ values in methanol ranged between 0.34 and 1.24 whereas in DMF they were between 0.85 and 1.88. The values of ΔS≠ favor a bimolecular rate-limiting step mechanism. Key words: nucleophilic addition to acetylenic esters.
1979 ◽
Vol 44
(3)
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pp. 912-917
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1991 ◽
Vol 56
(8)
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pp. 1701-1710
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1998 ◽
Vol 62
(23-24)
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pp. 3789-3790
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1997 ◽
Vol 61
(18)
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pp. 3897-3904
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1989 ◽
Vol 164
(Part_2)
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pp. 1121-1122
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1990 ◽
Vol 55
(6)
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pp. 1535-1540
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1988 ◽
Vol 53
(12)
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pp. 3154-3163
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