CHEMICAL REACTIONS OF THE NITROGEN MUSTARD GASES.<sup>1</sup> I. THE TRANSFORMATIONS OF METHYL-BIS(β-CHLOROETHYL)AMINE IN WATER

Golumbic, Calvin; Fruton, Joseph S.; Bergmann, Max

doi:10.1021/jo01175a015

Cited by 145 publications

(55 citation statements)

References 7 publications

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“…Should the rings have been opened by carbon disulfide, the C-H stretching frequencies would be expected at lower energies. Since there are no N-H bonds in products 1 and 2, as there are in the parent compounds and in 2-thiazolidinethione complexes, it is concluded that ~i ( a z ) , , ,~+ and Ni(meaz),,+ undergo carbon disulfide ~nsertion reactions [3] to provide dithiocarbamates as has been reported previously for other nickel(I1)-amine complexes (10).…”

Section: Resultssupporting

confidence: 68%

“…H2C-S A similar reaction occurs with 2-methylaziridine (3,4), although it has been reported in the patent literature that dithiocarbamate salts can be obtained from 2-methylaziridine, carbon disulfide, and base (5,6 can be prepared directly from many amine complexes by carbon disulfide insertion reactions (7-lo), it was of interest to investigate the reaction of carbon disulfide with aziridines coordinated to a metal ion. We report here the results of these investigations and some tentative conclusions concerning the structure of the unusual compounds formed.…”

Section: H2c'mentioning

confidence: 99%

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The Reaction of Carbon Disulfide with Aziridine Complexes of Nickel(II)

McCormick¹,

Kaplan²,

Stormer³

1971

Can. J. Chem.

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Carbon disulfide has been shown to undergo insertion reactions with [Ni(a~iridine),,~]'+ and [Ni(2-methyla~iridine),]~+.The diamagnetic products are formulated as planar dithiocarbamate complexes in which the heterocyclic ring remains intact. The complexes have properties whichare atypical of all dithiocarbamate complexes heretofore reported, and infrared and optical spectral measurements suggest that the insertion products may be the first examples of N,S-bonded dithiocarbamate ligands. In methanol the products slowly rearrange to give S,S-bonded complexes in which the aziridine rings have been opened.

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Section: Resultssupporting

confidence: 68%

Section: H2c'mentioning

confidence: 99%

The Reaction of Carbon Disulfide with Aziridine Complexes of Nickel(II)

McCormick¹,

Kaplan²,

Stormer³

1971

Can. J. Chem.

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“…Aqueous solvolysis of these compounds has been abundantly shown to involve a reactive though isolable ethylenimonium ion intermediate, XCIII (44,52,53,150,271,283,284,306,323,572,573,574,625).…”

Section: Solvolyeie(b)mentioning

confidence: 99%

Solvolytic Displacement Reactions At Saturated Carbon Atoms

1956

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“…The pH of the solution was 8.6; undue polymerization was thus avoided. After storage at 30°or 37°for 24 hours over 90 per cent of the total chlorine was found to be in the ionic form when titrated with silver nitrate (Golombic, Fruton and Bergmann, 1946 (Peterson and Greenberg, 1952) Radioactive chromatogramn, were exposed to Ilfex film.…”

Section: Methodsmentioning

confidence: 99%

The Distribution of Radioactivity in Tissues of the Rat Following the Administration of a Nitrogen Mustard Derivative

Cohn¹

1957

Br J Cancer

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AMINO ACIDS bearing the "nitrogen mustard" di-(2-chloroethyl)amino-side chain have been found to be effective inhibitors of the Walker carcinoma (Haddow, private communication; cf. Bergel and Stock, 1953). Their biological and chemotherapeutic behaviour is similar to that of other "nitrogen mustards" such-as di-(2-chloroethyl)methylamine itself. But special interest attached to one of these substituted amino acids, p-di-(2-chloroethyl)aminophenylalanine (Bergel and Stock, 1954), because its L-isomer was observed to be more active against the experimental tumour than the D-isomer (Haddow, private communication; cf. Bergel and Stock, 1953;Koller and Veronesi, 1956). This difference indicated that the configuration of the amino acid portion of the molecule might play a part in determining the mode of action of p-di-(2-chloroethyl)aminophenylalanine.The particular activity of the L-isomer, furthermore, suggested the possibility that this compound might influence protein formation or actually be incorporated into proteins. In the present investigation experiments were initially designed to test the occurrence of such incorporation with the aid of p-di-(2-chloroethyl)amino-DL-phenyl[fi-14C]alanine (PAM;Bergel, Burnop and Stock, 1955). In order to obtain precise information as to the origin of the different behaviours of the Dand L-forms it would clearly be desirable to do similar experiments with these forms. Unfortunately, the resolution of the DL-compound has not been achieved with the radioactively-labelled material. However, the work gave information in general on the distribution in the rat of a therapeutically effective nitrogen mustard derivative. MATERIALS AND METHODSAnimals and administration of PAM.-Male Wistar albino rats kept on a standard diet were injected intraperitoneally with PAM either suspended in arachis oil (8 mg./ml.) or as the sodium salt. This was freshly prepared by dissolving the acid in slightly less than the theoretical quantity of NaOH in methanol. The methanol was removed under slightly reduced pressure and NaCl

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CHEMICAL REACTIONS OF THE NITROGEN MUSTARD GASES.¹ I. THE TRANSFORMATIONS OF METHYL-BIS(β-CHLOROETHYL)AMINE IN WATER

Cited by 145 publications

References 7 publications

The Reaction of Carbon Disulfide with Aziridine Complexes of Nickel(II)

The Reaction of Carbon Disulfide with Aziridine Complexes of Nickel(II)

Solvolytic Displacement Reactions At Saturated Carbon Atoms

The Distribution of Radioactivity in Tissues of the Rat Following the Administration of a Nitrogen Mustard Derivative

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CHEMICAL REACTIONS OF THE NITROGEN MUSTARD GASES.1 I. THE TRANSFORMATIONS OF METHYL-BIS(β-CHLOROETHYL)AMINE IN WATER

Cited by 145 publications

References 7 publications

The Reaction of Carbon Disulfide with Aziridine Complexes of Nickel(II)

The Reaction of Carbon Disulfide with Aziridine Complexes of Nickel(II)

Solvolytic Displacement Reactions At Saturated Carbon Atoms

The Distribution of Radioactivity in Tissues of the Rat Following the Administration of a Nitrogen Mustard Derivative

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CHEMICAL REACTIONS OF THE NITROGEN MUSTARD GASES.¹ I. THE TRANSFORMATIONS OF METHYL-BIS(β-CHLOROETHYL)AMINE IN WATER