J. Am. Chem. Soc.

1951

DOI: 10.1021/ja01147a058

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Allylic Rearrangements. XXXI. The Reaction of Butenyl Chlorides with Diethylamine and Triethylamine

William G. Young¹,

Irving D. Webb²,

Harlan L. Goering³

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Synthesis Of Pdcp Ppobadeap Phebdeap and Pespobp1

Solvolysis Of Allylic Compounds: Literature Survey1

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Cited by 40 publications

(21 citation statements)

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“…It also reacts and converts into diethylamine. The convergence of TEA into diethylamine was confirmed by various researchers [44][45][46]. The presence of peaks at δ 1.16 and 3.07 showed the formation of diethylamine, as shown in Scheme 1 and Figure S1.…”

Section: Synthesis Of Pdcp Ppobadeap Phebdeap and Pespobpmentioning

confidence: 67%

Sustained release of hydrophilic drug from polyphosphazenes/poly(methyl methacrylate) based microspheres and their degradation study

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et al. 2016

Materials Science and Engineering: C

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No abstract

“…It also reacts and converts into diethylamine. The convergence of TEA into diethylamine was confirmed by various researchers [44][45][46]. The presence of peaks at δ 1.16 and 3.07 showed the formation of diethylamine, as shown in Scheme 1 and Figure S1.…”

Section: Synthesis Of Pdcp Ppobadeap Phebdeap and Pespobpmentioning

confidence: 67%

Sustained release of hydrophilic drug from polyphosphazenes/poly(methyl methacrylate) based microspheres and their degradation study

¹

,

²

,

³

et al. 2016

Materials Science and Engineering: C

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“…showed the presence of (4a) and the 1 : 1 adduct (7a) (peak area ratio 1 : 10); compound (4a) was identical with an authentic sample in respect of g.c. retention time and mass spectrum; compound (7a) was identified from its mass spectrum; m/z 255 ( M + , 317;), 214 (84), 196 (M -CO,Me, loo), 168 (21), 166 (30), 136 (40), 108 (38), 80 (33), and 59 (63) (Found: M + , 255.1462. C,3H2 1 N 0 4 requires M + , 255.1470).…”

Section: Resultsmentioning

confidence: 99%

Reactions of tertiary allylamines with dimethyl acetylenedicarboxylate

1987

J. Chem. Soc., Perkin Trans. 1

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The reaction of some tertiary allylamines with dimethyl acetylenedicarboxylate in acetonitrile results in the formation of 1 : 1 adducts via [3,3] rearrangement of the ally1 group from nitrogen to carbon.Tertiary amines catalyse the nucleophilic addition of species HX to activated acetylenes.' In some other cases, adducts incorporating the amine moiety are obtained as the result of C-N bond cleavage. Winterfeldt has described a variety of such reactions involving the tertiary amino-ester (la) and -ketones (lb) and (2) with methyl propiolate to give p-aminocrotonates (3a) and (3b).' The formation of N-ethylpyrrole derivatives from tertiary amines (lb) and (lc) and acetylene esters involves loss of the second N-ethyl group in each case. Similarly triethylamine is reported to add to dimethyl acetylenedicarboxylate (DMAD) in the presence of a proton source to give compound (4a), for which the maleate configuration, not assigned at the time, is correct by comparison of spectral data with those of analogous corn pound^.^^^ N-Benzylaziridine catalyses the trimerisation of DMAD in aprotic solvents, but in t-butyl alcohol a 1: 1: 1 adduct (4c) is obtained through opening of the aziridine ring.' Meo2c&ozMe Et ,NCH2 R ( 1 ) a; R = CH,CO,Et H NR' R' 1 2 b; R = COPh ( 4 ) a; R = R = E t c; R = C02Me b; R ' , R 2 = (CH,), 1 C; R = CHZPh, R2= C H 2 C H 2 0 8~' d; R'= R2= Me 1 2 e; R , R =(CH212 1 2 1 2 ( C N C ti 2 c H 2)0 f ; R , R = CHzCH=CHCH2 9; R , R = (CH,),R1R2NCH=CHC02Me 1 2 1 ( 3 ) a; R = R = Et b; R , R 2 = (CH215 the same derivative (9b). Authentic samples of the by-products (4a) and (4b) were prepared from DMAD with diethylamine and piperidine, respectively, and similarly converted into the 2,4-dinitrophenylhydrazone derivative (9a). Catalytic hydrogenation of the adduct (7a) gave the corresponding propyl compound (8), which was characterised both as the 2,4-dinitrophenylhydrazone (9d), and by degradation to 2-oxohexanoic acid (Scheme 2). Me02C , C0,Me \ %+ , R1 R'R2NCH2CH=CHR3 -R37(&J,R2 ( 6 ) ( 5 ) a ; R 1 2 = R = E t , R 3 = H c ; R 1 = R 2 = Et, R 3 = Me I b; R', R2 = (CH2I5, R 3 = H Pd I H2 ( 7 a I -CH 1 3 ( 7 ) a ; R = R2= Et, R = H b; R', R 2 = (CH215, R 3 = H 1 c; R = RZ= Et, R3= Me Scheme 1. M e o z c~c o 2 N e -H~O + BuCOC02H Pr NEt, ( 8 1 Scheme 2.Me0,C COzMe Me02C \ /CO2Me Results and DiscussionWe have examined the addition of tertiary allylic amines to DMAD. Although no reaction occurs between allyldiethylamine (5a) and DMAD in dry ether, these compounds react readily in acetonitrile at room temperature to give the 1: 1 adduct (7a) together with smaller amounts of the aminomaleate ( 9 a; = (4a). The proportion of (4a) increased if water was added to the product (7a) even when thoroughly dry acetonitrile was used. the 1: 1 adduct (7b) and a smaller amount of (4b). The constitution of the adducts (7a) and (7b) was proved from their 'H n.m.r. and mass spectra and by hydrolysis in the presence of a x ; : //C -CH Me 2 , 4 -( 0 ,~ ),C~H,NHN ' R (10) system, but it still amounted to a small percentage of the m...

“…However, in the reaction of a-methylallyl chloride with triethylamine or trimethylamine without solvent under relatively mild reaction conditions it was demonstrated that abnormal dasplacement (SN2) occurred preferentially to normal displacement (SN2) (9,10). In the reaction of alkylallyl chlorides with longer alkyl chains, this tendency is considered to be more remarkable because of steric hindrance.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of cationic surfactants with alkenyl group

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et al. 1973

J Americ Oil Chem Soc

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Quaternary ammonium chlorides with long chain alkenyl groups were synthesized by the reaction of tert-amines with alkylallyl chloride which, in turn, were obtained by the allylic chlorination of l-olefins with N-tert-butyl-or N-cyclohexyl-N-ehloro-ethanesulfonamides. Of the two kinds of alkylallyl chlorides prepared by the allylic chlorination of 1-olefins, the 7-alkylallyt ctflorides(I), were found to be reactive with tert-amines, while the secondary chlorides, 0~-alkylallyl chlorides(II), were not so reactive and, when the allylic chloride mixture was reacted with tert-amine under suitable reaction conditions, the 7-alkylallyl chloride could be selectively converted to a quaternary ammonium chloride while the a-alkylallyl chloride was recovered unreacted. The quaternary ammonium chlorides thus obtained were identified as 7-alkylallyl ammonium chlorides from their spectra, and they were shown to possess almost the same surface tension lowering ability as their saturated homologs, although larger critical micelle concentration values and greater water solubilities were observed.

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