Stereoselectivity in the thermal rearrangement of 3,4-bistrimethylsiloxy-1,5-hexadiynes.

Manisse, N.; Chuche, J.

doi:10.1016/s0040-4039(00)75084-2

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Cited by 6 publications

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“…3,[13][14][15][16] Application of this finding to the present study shows that the 3,4-bis(methylene)-cyclobutenes in which the exocyclic double bonds are both E were produced from the diol racemates via racemic diallenes, while those in which one double bond is E and the other is Z originate in the meso diols via P,M-diallenes. The steps leading to the various isomers of 8 and 9 are shown in Scheme 3.…”

Section: Introductionsupporting

confidence: 58%

Electron depleted bis(methylene)cyclobutenes: sulfinyl and sulfonyl substitution

et al. 2005

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Section: Introductionsupporting

confidence: 58%

Electron depleted bis(methylene)cyclobutenes: sulfinyl and sulfonyl substitution

et al. 2005

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Thermal Rearrangements, XXII. The Propargyl‐Cope Rearrangement of meso‐ and d,l‐3,4‐Dimethyl‐1,5‐hexadiyne‐3,4‐diol

et al. 1994

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The thermal behavior of meso‐ and d,1‐3,4‐dimethyl‐1,5‐hexadiyne‐3,4‐diol (meso‐ and d,1–4) has been studied at 400°C in the gas phase. In a tandem reaction the diols isomerize via the bisallenes 5 first to cis‐ and trans‐3,4‐diacetylcyclobutene (cis‐ and trans‐8) which have been detected as intermediates by 13C‐NMR spectroscopy as well as catalytic hydrogenation to 1,2‐diacetylcyclobutane (9). Subsequently, 8 stabilizes itself by ring opening to (E,Z)‐ and (E,E)‐3,5‐octa‐dien‐2,7‐dione (E,Z) and [(E,Z)‐6]. As a side reaction retroene cleavage of 4 to 2‐butynone (10) and methyl vinyl ketone (12) is observed. By pyrolysis of the pure diastereomers 4 it is shown that the retro‐ene process is more pronounced in the d,l than in the meso series.

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ChemInform Abstract: STEREOSELECTIVITY IN THE THERMAL REARRANGEMENT OF 3,4‐BISTRIMETHYLSILOXY‐1,5‐HEXADIYNES

MANISSE¹,

Chuche²

1975

Chemischer Informationsdienst

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Stereoselectivity in the thermal rearrangement of 3,4-bistrimethylsiloxy-1,5-hexadiynes.

Cited by 6 publications

References 12 publications

Electron depleted bis(methylene)cyclobutenes: sulfinyl and sulfonyl substitution

Electron depleted bis(methylene)cyclobutenes: sulfinyl and sulfonyl substitution

Thermal Rearrangements, XXII. The Propargyl‐Cope Rearrangement of meso‐ and d,l‐3,4‐Dimethyl‐1,5‐hexadiyne‐3,4‐diol

ChemInform Abstract: STEREOSELECTIVITY IN THE THERMAL REARRANGEMENT OF 3,4‐BISTRIMETHYLSILOXY‐1,5‐HEXADIYNES

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