The Preparation of Cyclopropene

Schlatter, Maurice J.

doi:10.1021/ja01851a068

Cited by 47 publications

(14 citation statements)

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“…[5] 49"C/750 Torr). The compound obtained in this way gave only one peak when chromatographed on 5-m columns containing Apiezon L, dinonyl phthalate, or polyethylene glycol, all on Celite at 140°C.…”

Section: B Materialsmentioning

confidence: 99%

“…Cyclopropylamine (Koch-Light Laboratories Ltd.), distilled through a 1-m Buchi spinning band column, had bp 49.5"C/755 Torr (lit. [5] 49"C/750 Torr). The compound obtained in this way gave only one peak when chromatographed on 5-m columns containing Apiezon L, dinonyl phthalate, or polyethylene glycol, all on Celite at 140°C.…”

Section: B Materialsmentioning

confidence: 99%

“…(5):loglo(kI/s-') = (15.06 f 0.41) -(242.0 f 2.6) kJ mole-'/2.303RT(5) R = Et, n-Pr, iPr, NHa + EtCH=NR I + RNHz allyl, ~-C~H & '…”

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confidence: 99%

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Kinetics of the reactions of cyclopropane derivatives, part II. The gas‐phase pyrolysis of cyclopropylamine

Parry

Robinson

1973

Int J of Chemical Kinetics

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At temperatures of 356-425°C and pressures of 1 5 6 0 Torr, cyclopropylamine reacts to give an equimolar mixture of ammonia and N-propylidenecyclopropylamine as the initial product. The reaction is first order, homogeneous, and unaffected by the presence of radical inhibitors, and thus proceeds by an initial ratedetermining unimolecular isomerization to give a reactive intermediate, which then reacts with a further molecule of cyclopropylamine to give the observed products. Reaction in the presence of added aliphatic amines gives other imines in addition, and the nature of these indicates that the intermediate is propenylamine or its tautomer propylideneamine:

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Section: B Materialsmentioning

confidence: 99%

Section: B Materialsmentioning

confidence: 99%

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Kinetics of the reactions of cyclopropane derivatives, part II. The gas‐phase pyrolysis of cyclopropylamine

Parry

Robinson

1973

Int J of Chemical Kinetics

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“…Absorption spectra were obtained using a Beckman Model DU Spectrophotometer. The pyrolyses were carried out in an apparatus similar to that used previously in this Laboratory (15). The decomposition chamber was prepared by blowing a test-tube bottom on the female half of a 24/40 standard taper joint to give a tube 11 cm.…”

Section: Experimental Partmentioning

confidence: 99%

The Thermal Decomposition of Allyltrimethyl-Ammonium Hydroxide

Howton¹

1949

J. Org. Chem.

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Current studies in this Laboratory involve the thermal decomposition of certain allylic trimethylammonium hydroxides. The observation that quite appreciable amounts of dimethylamine and saturated carbonylic compounds are formed in these reactions has led to the belief that these quaternary bases rearrange to some extent during the pyrolysis, giving vinylic trimethylammonium bases. Although it is conceivable that the carbonylic products might be formed by the rearrangement of allylic alcohols derived from the unrearranged quaternary bases, the only readily understood mechanism by which dimethylamine could be formed involves the hydrolysis of a vinyldimethylamine, formed by an Sn2 attack by hydroxyl ion upon a methyl group of the vinyltrimethylammonium ion. The products of such a reaction would be methanol and a vinyldimethylamine, which would be hydrolyzed (in the dilute acid commonly used to absorb the bases formed in Hofmann degradations) to dimethylamine and a saturated carbonylic compound.1 2 A thorough examination of the products formed in the thermal decomposition of the simplest allylic trimethylammonium hydroxide (I) was considered worth while to substantiate these findings and postulates.The pyrolysis of I has not been studied for over half a century,3 and then only cursorily. In an obscure publication which appeared in 1886 and has since been overlooked or discredited, Bono (3) heated allyltrimethylammonium iodide with potassium hydroxide and obtained an aldehyde, CeHioO, whose boiling point, 130-135°( as he pointed out) corresponded to that of a-methyI-/3-ethylacrolein (IV), the only aldehyde of that formula known at that time; since our findings (see below) substantiate Bono's identification of this product,4 the question mark appearing in Beilstein's account (5) of his work should be deleted. A short time

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“…Cyclopropene is known to dimerize and polymerize at room temperature [26,27]. Substituted cyclopropenes are generally more stable.…”

Section: Introductionmentioning

confidence: 99%

The reactivity of TMSN3 with ruthenium cyclopropenyl complexes containing different ligands and different substituent at Cγ

Sung

Hsu

2011

Journal of Organometallic Chemistry

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The Preparation of Cyclopropene

Cited by 47 publications

References 0 publications

Kinetics of the reactions of cyclopropane derivatives, part II. The gas‐phase pyrolysis of cyclopropylamine

Kinetics of the reactions of cyclopropane derivatives, part II. The gas‐phase pyrolysis of cyclopropylamine

The Thermal Decomposition of Allyltrimethyl-Ammonium Hydroxide

The reactivity of TMSN3 with ruthenium cyclopropenyl complexes containing different ligands and different substituent at Cγ

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