Clam Poison: Iii. Paper Electrophoresis of Clam Poison

Bannard, R. A. B.; Casselman, A. A.

doi:10.1139/v62-249

Cited by 6 publications

(10 citation statements)

References 6 publications

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“…One of these, the last to be accomplished, has already been published in another connection (19).3 The other, earlier proofs remain separately valid, add independent support to that already given (19), and are interesting in respect to the chemistry of cyclopentane.…”

Section: Proofs Of Structurementioning

confidence: 59%

“…The chlorohydrin thought to be 9 was dehalogenated by the method described previously (19) to give amethoxycyclopentanol(12) which proved to be identical with authentic trans-2-methoxycyclopentanol (20) made by the alkali-catalyzed methanolysis of cyclopentene oxide. This settled 4Space does not permit a full outline of the argument.…”

Section: Proofs Of Structurementioning

confidence: 99%

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Epoxides and trans-chlorohydrins of 3-methoxycyclopentene and their use in conformational studies in the cyclopentane system

Langstaff¹,

Moir²,

Bannard³

et al. 1968

Can. J. Chem.

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The stereoisomeric oxides of 3-methoxycyclopentene (3 and 4) and the four trans-chlorohydrins of the same olefin ( 6 9 ) were prepared by methods resembling those used previously in the cyclohexane system. Structure proofs were more difficult than in the cyclohexanes, but served to illustrate some interesting chemistry. Product ratios in the cleavage of each of the epoxides with hydrogen chloride were used to deduce the probable conformations of the four transition states, by comparing the results with those from the cyclohexane system. An unexpected outcome of the work was the new convincing evidence obtained for the intervention of chloronium ions in the addition of "hypochlorous acid" to the olefin.

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Section: Proofs Of Structurementioning

confidence: 59%

Section: Proofs Of Structurementioning

confidence: 99%

Epoxides and trans-chlorohydrins of 3-methoxycyclopentene and their use in conformational studies in the cyclopentane system

Langstaff¹,

Moir²,

Bannard³

et al. 1968

Can. J. Chem.

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“…Mousseron, Bodot, and co-workers (10, 11) have used the reversibility of the first step in Scheme 1 (that is, the external return of the nucleophile) in gaining indirect evidence for the presence of intermediates analogous to 6. Under the conditions of our solvolyses, this reversibility was suppressed, along with the consequent rearrangement pathway (22,23):…”

mentioning

confidence: 89%

“…If a protonated epoxide is an intermediate in solvolysis with neighboring trans hydroxyl, then 6 is the common intermediate in the solvolyses of 5,7a, and 8a. In previous work we had shown (22) that the acid-catalyzed methanolysis of 5 gave two products, 9a and IOU, the former predominating greatly. If a protonated epoxide is an intermediate, then methanolysis of the oxide 5 and of each of the tosylates 7a and 8a should give both 9a and IOU.…”

mentioning

confidence: 96%

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Migration of hydroxyl in secondary systems during solvolysis in acid solution

Cathcart¹,

Bovenkamp²,

Moir³

et al. 1977

Can. J. Chem.

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Can. J. Chem. 55,3774 (1977). A system of compounds has been prepared which is well adapted for displaying the role of trans vicinal, secondary hydroxyl in solvolysis. On methanolysis in acid solution, compounds 5, 7a, and 8a all gave the same products, 9a and 10a, and in practically the same proportions, suggesting that at least one intermediate was common to all three reactions. These intermediates were such that 7a and 8u were not interconverted during the solvolysis, a fact in support of 6 as a common intermediate. Several alternative explanations were shown to be untenable, largely by taking advantage of the remarkable differences between hydroxyl and methoxyl. The work provides the most decisive evidence available for the covalent participation of hydroxyl as a neighbor group in the solvolysis of secondary systems, and contributes also to the study of the reverse reaction, the acid-catalyzed scission of epoxides. On prepare un systeme de composes lequel est bien adapte pour mettre en evidence le r61e du groupe hydroxyle trans vicinal dans des reactions de solvolyse. La mkthanolyse en solution acide des composks 5, 7a et 8a conduit aux mCmes produits 9a et 10a et essentiellement aux m&mes proportions suggerant qu'au moins un intermediaire est commun aux trois reactions. Ces intermediaires sont de telle sorte que 7a et 8a ne sont pas convertis I'un dans I'autre pendant la solvolyse, ce qui est en accord avec l'hypothese que 6 soit un intermediaire commun. Plusieurs interprktations ne peuvent Ctre soutenues, essentiellement parce qu'elles ne tiennent pas compte des grandes differences entre un groupe hydroxyle et methoxyle. Ce travail apporte l'evidence tres nette de la participation covalente du groupe hydroxyle comme groupe voisin dans la solvolyse de systemes secondaires et contribut aussi a l'etude de la reaction inverse, la scission catalyske par un acide des Cpoxydes.[Traduit par le journal]

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The Chemistry of Toxins Isolated from Some Marine Organisms.

Scheuer

1964

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès Dans La Chimi

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Clam Poison: Iii. Paper Electrophoresis of Clam Poison

Abstract: 111 paper strip electrophoretograms on Whatman 3MM paper, clam poison migrated toward the cathode when forrnic acid (1 IV and 0

Cited by 6 publications

References 6 publications

Epoxides and trans-chlorohydrins of 3-methoxycyclopentene and their use in conformational studies in the cyclopentane system

Epoxides and trans-chlorohydrins of 3-methoxycyclopentene and their use in conformational studies in the cyclopentane system

Migration of hydroxyl in secondary systems during solvolysis in acid solution

The Chemistry of Toxins Isolated from Some Marine Organisms.

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