Lactam acetals

Граник, В. Г.; Zhidkova, A. M.; Vlasova, T. F.; Глушков, Р. Г.; Sheinker, Yu. N.

doi:10.1007/bf00945642

Cited by 2 publications

(3 citation statements)

References 2 publications

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“…Substituting an olefinic hydrogen for an alkyl group affects the oxidation potential in the same direction, albeit to a lesser degree. * For this reason, the ketene aminal( 2) is expected to be a better electron donor than ketene aminal (6). As was shown above, our results of the reactions of (1) and ( 5 ) with CCI, in D M F indicate this behaviour.…”

Section: The Halogenationsupporting

confidence: 83%

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Solvent- and reagent-induced change of rate-limiting step in acid-catalysed α-halogenation of amidines with tetrahalogenomethanes

Löfås¹,

Ahlberg²

1986

J. Chem. Soc., Perkin Trans. 2

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Section: The Halogenationsupporting

confidence: 83%

“…An investigation of the deuteriation of 1 -methyl-2-aroyliminolactams in CD,OD at 70 "C showed that the rate of deuterium incorporation was dependent on the ring size. The six-membered ring was deuteriated four and eight times faster than the five-and seven-membered ring systems, respectively 6.…”

mentioning

confidence: 94%

Solvent- and reagent-induced change of rate-limiting step in acid-catalysed α-halogenation of amidines with tetrahalogenomethanes

Löfås¹,

Ahlberg²

1986

J. Chem. Soc., Perkin Trans. 2

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“…We conclude that metal hydrides with larger ligands make pathway B more competitive and with smaller ligands favour pathway C. L-Selectride possesses medium-sized ligands and served as the best reducing agent for (19).…”

Section: Discussionmentioning

confidence: 86%

New method for the selective reduction of amides

Tsay¹,

Robl²,

Hwu³

1990

J. Chem. Soc., Perkin Trans. 1

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A new procedure was developed for the reduction of tertiary aliphatic, olefinic, and aromatic amides t o aldehydes. Reaction of the amides (1)' (5), ( 7 ) , (9), (ll), ( 13), (15), and (17) with ethyl or methyl trifluoromethanesulphonate in CH,CI, at room temperature and then with L-Selectride at -78°C gave the corresponding aldehydes (2), ( 6) , (8), (lo), (12), ( 14), ( 16), and (18), respectively. A second functional group, including C02R, G C , CH(OCH,CH,O), and C=N, in these amides was found to be inert under the conditions employed. These selective reductions gave the desired aldehydes in 50-73% isolated yields and in > 95% yields based on converted amides.Amides can be converted into aldehydes in satisfactory yields by several reducing agents, such as LiA1H4,lp3 LiAlH(OEt)3,4*5 and NaAlH,(OCH,CH,0Me)2.6 Only a few procedures however can lead to aldehydes efficiently by reduction of amides that contain other readily reducible functional groups.' We now report a solution to this problem by use of alkyl trifluoromethanesulphonates and L-Selectride.

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Lactam acetals

Cited by 2 publications

References 2 publications

Solvent- and reagent-induced change of rate-limiting step in acid-catalysed α-halogenation of amidines with tetrahalogenomethanes

Solvent- and reagent-induced change of rate-limiting step in acid-catalysed α-halogenation of amidines with tetrahalogenomethanes

New method for the selective reduction of amides

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