T-butyrolactone

H-ZSM-5 impregnated with Cr catalyzes syntheses of five- and six-membered heterocycles. For example, T butyrolactone and methylamine are converted to l-methyl-2-pyrrolidone with 98.2% yield [80]. 

N-Acetylamino-L-tryptophane, 530 17a-Acetyl-A -androstene-3/5,l 7 S-diol, 660 9-Acetylanthracene, 27, 131 a-Acetyl-T-butyrolactone, 676 Acetyl chloride, 11, 263-264, 275, 336 2-, 4-, and 5-Acetylchrysene, 676-677 S-Acetylcoenzyme A, 1157... 

Protection of a-methylene-f-butyrolactones. Sodium thiophenoxide undergoes Michael addition to a-methylene-T-butyrolactones in nearly quantitative yield. Deblocking involves oxidation of the sulfide to the sulfoxide and thermal elimination of benzenesulfenic acid. The yield in all steps is high. ... 

Singh, L., Donald, A. E., Foster, A. C. Enantiomers of HA-966 (3-amino-l-hydroxypytrolid-2-one) exhibit distinct central nervous system effects (+)-HA-966 is a selective glycine/N-methyl-D-aspar-tate receptor antagonist, but (-)-HA-966 is a potent t-butyrolactone-Uke sedative. Proc. Natl. Acad. Sci. USA 1990,87, 347-351. 

PdCl- gives T-butyrolactones in moderate yield. Unfortunately... 

Starting from nucleic acid bases, the carboxyethyl derivatives of the nucleic acid bases were prepared by a Michael type addition reaction of ethyl acrylate followed by hydrolysis. The carboxyethyl derivatives of nucleic acid bases were reacted with ( )-a-amino T-butyrolactone hydrobromide to give v-hutyrolactone derivatives of nucleic acid bases. For the coupling reactions, pentachlorophenyl ester derivatives were used with imidazole as a catalyst.22... 

For related sulfoxide to olefin transformations, see B. M. Trost and T. N. Saizmann, ). Amer. Chem. Soc., 95, 5321 (1973). Recently, P. A. Grieco and J. J. Reap (Tetrahedron Lett., 1097 (1974)] have reported a novel a-methylenation sequence, based on the thermal elimination of a-phenylsulfinyl lactones to a-methylene-T-butyrolactones (i-4i). 

Diethyl oxalate Diethyl malonate Diethyl succinate Diethyl adipate Diethyl maleate Diethyl fumarate d-Propiolactone T/-Butyrolactone 5-Valerolactone Ethyl dlchloroacetate Ethyl trichloroacetate... 

Hydrazoic acid reaction with cyclobu-tanecarboxyhc acid, 47, 28 Hydrogenation of t butylazidoacetate to glycme ( butyl ester, 46,47 Hydrogen bromide 46, 43 reaction with y butyrolactone, 46, 43 Hydrogen fluoride anhydrous, precautions in use of, 46, 3 in preparation of mtromum tetra-fluoroborate 47, 57 reaction with benzoyl chloride, 46,4 with boron tnfluonde in conversion of p cymene to m cymene, 47, 40 in bromofluorination of 1 heptene, 46, 11... 

Limited progress has been achieved in the enantioselective hydrogenation of a,/ -unsaturated carboxylic acid esters, amides, lactones, and ketones (Scheme 26.10). The Ru-BINAP system is efficient for the hydrogenation of 2-methy-lene-y-butyrolactone, and 2-methylene-cyclopentanone [98]. With a dicationic (S)-di-t-Bu-MeOBIPHEP-Ru complex under a high hydrogen pressure, 3-ethoxy pyr-rolidinone could be hydrogenated in isopropanol to give (R)-4-ethoxy-y-lactam in 98% ee [39]. 

B. D. Andresen, F. T. Davis, J. L. Templeton, R. H. Hammer, H. L. Panzik, Synthesis and Characterizaiton of a/p/za-Phenyl-garona-Butyrolactone, a Metabolite of Glutethi-mide, Phenobarbital and Primidone, in Human Urine , Res. Commun. Chem. Pathol. Pharmacol. 1976, f J, 21 - 30. 

A parallel study [94] was performed by the same authors on the retention of model compounds (tryptophan, erythro- and t/ireo-P-methyltryptophan, A-carbobenzyloxy-tryptophan, A-(3,5-dinitro-2-pyridyl)-tryptophan, l-[5-chloro-2-(methylamino) phenyl]-l,2,3,4-tetrahydroisoquinoline, and y-phenyl-y-butyrolactone) on a ristocetin A-based CSP, using the three RP, POM, and NP elution systems. Also, in this case, the natural logarithms of the retention factors (In k) of the investigated compounds depended linearly on the inverse of temperature (1 /T). 

Bjola, B.S., Siddiqi, M.A., and Svejda, P. Excess enthalpies of binary liquid mixtures of y-butyrolactone + benzene. + toluene, -t ethylbenzene, and -t carbon tetrachloride, and excess volume of the y-butyrolactone + carbon tetrachloride liquid mixture, / Chem. Eng. Data, 46(5) 1167-1171, 2001. 

Urban T (2007) PhD Thesis. Neue chirale Katalysatorsysteme zur Synthese von enantiomer-enangereichertem beta-Butyrolacton aus Propylenoxid und CO. Universitat Ulm, Ulm... 

Amgoune A, Thomas CM, Ilinca S, Roisnel T, Carpentier J-F (2006) Highly active, productive, and syndiospeciflc yttrium initiators for the polymerization of racemic (3-butyrolactone. Ang Chem Int Ed 45 2782-2784... 

The 4-hydroxy-1-alkene (homoallylic alcohol) 81 is oxidized to the hemi-acetal 82 of the aldehyde by the participation of the OH group when there is a substituent at C3. In the absence of the substituent, a ketone is obtained. The hemiacetal is converted into butyrolactone 83[117], When Pd nitro complex is used as a catalyst in /-BuOH under oxygen, acetals are obtained from homoallylic alcohols even in the absence of a substituent at C-3[l 18]. t-Allylamine is oxidized to the acetal 84 of the aldehyde selectively by participation of the amino group[l 19]. 

Higgins,T.F. Borron, S.W. (1996) Coma and respiratory arrest after exposure to butyrolactone. 

FIGURE 6 Effect of mobile phase composition on the resolution of enantiomers of different racemates in normal phase HPLC on antibiotic CSPs. (a) First ( ) and second ( ) eluted enantiomers of y-phenyl-y-butyrolactone and first ( ) and second (O) eluted enantiomers of 4-phenyl-2-methoxy-6-oxo-2,4,5,6-tetrahydropyridine-3-carbonitrile on Chirobiotic T column and (b) first ( ) and second (O) eluted enantiomers of mephenytoin on Chirobiotic V column. (From Refs. 1 and 21.)... 

Toda, F., Tanaka, K., Omata, T., Nakamura, K., and Oshima, T. (1983) Optical Resolution of 3-Methylcyclohexanones and 5-Methyl- -butyrolactone by Complexation with Optically Active 1,6-Bis(o-halopheny 1)-1,6-diphenylhexa-2,4-... 

Beugelmans, R. Amrollah-Madjdabadi, A. Frinault, T. Morris, A. D. Gharbaoui, T. Benhida, R. Lechevallier, A. New and straightforward access to olefins, butenolides and /3-nitro y-butyrolactones from precursors obtained via SrnI reactions. Bull. Soc. Chim. Fr. 1994, 333, 1019-1030. 

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