Stereochemistry of 1,4-Addition. I. The Chlorination of Butadiene<sup>1</sup>

Mislow, Kurt; Hellman, Henry M.

doi:10.1021/ja01145a083

Cited by 27 publications

(4 citation statements)

References 2 publications

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“…The action of anhydrous hydrogen bromide on the ethyl ether of a-phenethyl alcohol has been investigated (194). S o a-phenethyl alcohol was detected in the reaction products, which consisted of ethyl ether, ethyl bromide, ethanol, styrene, and a-phenethyl bromide.…”

Section: Further Descriptive Chemistry Of Cleavage By Hydrogen Hamentioning

confidence: 99%

Cleavage of Ethers

1983

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Section: Further Descriptive Chemistry Of Cleavage By Hydrogen Hamentioning

confidence: 99%

Cleavage of Ethers

1983

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“…and 152.5°( 758 mm.). 6 This compound was also obtained in essentially the same yield when an excess of pyridine was used, and in 43% yield from the diol, phosphorus trichloride, and pyridine.5 l-Phenyl-3-pyrroline (II). A solution of 62.5 g. (0.5 mole) of cts-l,4-dichloro-2-butene in 40 ml.…”

Section: Methodsmentioning

confidence: 91%

Notes: Amination Reactions of cis-1,4-Dichloro-2-butene

Bobbitt¹,

Amundsen²,

Steiner³

1960

J. Org. Chem.

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Ammonia and amines with cis-1,4-dichloro-2butene produce cyclic products in contrast to their reactions with trans-1,4-dichloro-2-butene, which yield diamines or polyamines of high molecular weight. Although 3-pyrroline may be obtained from ammonia, the more readily obtainable product is a spiro compound formed by reaction of two moles of the dichloride with one mole of ammonia.cis-1,4-Dichloro-2-butene, I, reacts with ammonia and with amines to yield cyclic products. Thus, with the primary amine aniline, A-phenyl-3pyrroline, II, is formed, and with the secondary amine diethylamine, A,A-diethyl-3-pyrrolinium chloride, III, is formed and was isolated as its

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“…DL-2,6-Diamino-4-hexynoate (DL-lysyne) was synthesized according to the procedure of Jansen et al (1970). DL-m-2,6-Diamino-4-hexenoate (DL-m-lysene) was prepared by starting from 2-butene-1,4-diol (91% cis isomer; Aldrich) which was converted to the cis dichloride by using PC13pyridine as described by Mislow & Heilman (1951). Following fractional distillation of the dichloride under reduced pressure to yield the pure cis isomer (>99% pure by gas chromatography), m-4-lysene was prepared in essentially the same fashion as 4-lysyne.…”

Section: Methodsmentioning

confidence: 99%

Studies with mechanism-based inactivators of lysine .epsilon.-transaminase from Achromobacter liquidum

Shannon¹,

Coppersmith²,

Walsh³

1979

Biochemistry

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Analogues of lysine containing a 4,5-acetylenic linkage (lysyne) or a cis- or trans-4,5-olefinic linkage (lysenes) function as substrates for a homogeneous L-lysine epsilon-transaminase from Achromobacter liquidum but partition between transamination and time-dependent inactivation. The partition ratio is lowest for lysyne (40 per inactivation event) and higher for trans-lysene (160 per inactivation event), and the cis-lysene transaminates 1600 times per inactivation event. cis-Lysene yields alpha-picolinate as a detectable accumulating product, presumably from cyclization of initial 6-aldehyde to dihydropicolinate and spontaneous autoxidation. The trans isomer also yields some picolinate as an identifiable product. The product from the few lysyne turnovers is as yet unknown but has strong absorbance at 318 nm. The inactive enzyme species from all three lysine analogues slowly (overnight) regain full activity after gel filtration chromatography and dialysis, suggesting reversal of the initial adduct-forming reaction. Initial studies with partially purified pseudomonad lysine alpha-racemase show alpha-3H incorporation from 3H2O but no inactivation consistent with the expectation that these lysine analogues could act readily as mechanism-based inactivators for pyridoxal P enzymes which act at the epsilon- but not the alpha-carbon of lysine.

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Stereochemistry of 1,4-Addition. I. The Chlorination of Butadiene¹

Cited by 27 publications

References 2 publications

Cleavage of Ethers

Cleavage of Ethers

Notes: Amination Reactions of cis-1,4-Dichloro-2-butene

Studies with mechanism-based inactivators of lysine .epsilon.-transaminase from Achromobacter liquidum

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Stereochemistry of 1,4-Addition. I. The Chlorination of Butadiene1

Cited by 27 publications

References 2 publications

Cleavage of Ethers

Cleavage of Ethers

Notes: Amination Reactions of cis-1,4-Dichloro-2-butene

Studies with mechanism-based inactivators of lysine .epsilon.-transaminase from Achromobacter liquidum

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Stereochemistry of 1,4-Addition. I. The Chlorination of Butadiene¹