The Decomposition of Certain Acetylenic Carbinols

Thompson, A.; Margnetti, Charles

doi:10.1021/ja01255a032

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“…Such processes can lead to anomalous behavior at those extreme temperatures. In this regard, it is interesting to note that a number of alkynes containing the Me 2 (HO)C– moiety, like that present in 8 , are reported to fragment and liberate the terminal alkyne upon thermolysis at high temperatures (175–275 °C) . However, it can be concluded with confidence that neither of these bulky diynes shows any significant sign of reactivity below ca.…”

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Differential Scanning Calorimetry (DSC) as a Tool for Probing the Reactivity of Polyynes Relevant to Hexadehydro-Diels–Alder (HDDA) Cascades

Woods

Hoye

2014

Org. Lett.

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The differential scanning calorimetry (DSC) behavior of a number of alkyne-rich compounds is described. The DSC trace for each compound exhibits an exothermic event at a characteristic onset temperature. For the tri- and tetraynes whose [4 + 2] HDDA reactivity in solution has been determined, these onset temperatures show a strong correlation with the cyclization activation energy. The studies reported here exemplify how the data available through this operationally simple analytical technique can give valuable insights into the thermal behavior of small molecules.

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confidence: 97%

Differential Scanning Calorimetry (DSC) as a Tool for Probing the Reactivity of Polyynes Relevant to Hexadehydro-Diels–Alder (HDDA) Cascades

Woods

Hoye

2014

Org. Lett.

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The Synthesis of Acetylenes

Jacobs

2011

Organic Reactions

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Many advances have been made in recent years in the methods for the synthesis of acetylenes and many compounds are now rather readily available in the pure state. Acetylene was first prepared by Davy, who treated acetylide with water. Propyne, the first substituted acetylene was obtained in 1861. At the present time alkynes are usually synthesized by the alkylation of sodium acetylide or substituted metallic acetylides, often in liquid ammonia and 1‐Alkynes are also obtained by dehydrohalogenation of suitable halides with sodium amide or in certain cases by ethanolic alkali. The present discussion will be limited to methods for the creation of a carbon‐carbon triple bond and to the alkylation of metallic acetylides.

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Konstitution und Lichtabsorption, VI. Mitteil.: Zur Deutung von Polyacetylen‐Spektren, sowie Darstellung von Bis‐tert.‐butyl‐decapentain‐(1.3.5.7.9)

Bohlmann¹

1953

Chem. Ber.

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Durch Darstellung des bisher noch fehlenden Gliedes, einer Pentaacetylen-Verbindung, wurde die Reihe der Polyine vervollstilndigt. Die Unterschiede in den Spektren der Polyine gegeniiber denen der Polyene werden gedeutet. Die verschiedene Lage der Maxima kommt durrh die unterschiedlichen Bindungsabstiinde und die sich daraus ergcbenden Unterschiede in der Lange der x-Elektronenwolken zustande. Die grol3ere Intensitkit der Banden bei den Polyinen ergibt sich aus der erhohten tfbergangswahrschcinlichkeit. *) in HenzolEmpirisch war die 1,itge dcr Maxima bei den I'olyinen nach eineni IVurzelgeset.z h r-4 a -i I ) . I I ZII berechnen'): Es wurde nun nach einer theoretischen Deiitunp tler anomalen Absorptionsspektren in dieser Reihe gesucht .

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The Decomposition of Certain Acetylenic Carbinols

Abstract: It was purified by recrystallization from water, m. P. 156hvdroxide to retronecine and an acid not vet iso-157" (cor.) with decomposition.

Cited by 4 publications

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Differential Scanning Calorimetry (DSC) as a Tool for Probing the Reactivity of Polyynes Relevant to Hexadehydro-Diels–Alder (HDDA) Cascades

Differential Scanning Calorimetry (DSC) as a Tool for Probing the Reactivity of Polyynes Relevant to Hexadehydro-Diels–Alder (HDDA) Cascades

The Synthesis of Acetylenes

Konstitution und Lichtabsorption, VI. Mitteil.: Zur Deutung von Polyacetylen‐Spektren, sowie Darstellung von Bis‐tert.‐butyl‐decapentain‐(1.3.5.7.9)

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