ALKATRIENYL SULFOXIDES AND SULFONES. PART IV. SYNTHESIS AND ELECTROPHILEINDUCED CYCLIZATION REACTIONS OF 3-METHYL-1-METHYLSULFONYLPENTA-1,2,4-TRIENE

doi:10.1080/10426500490466265

Paper

ALKATRIENYL SULFOXIDES AND SULFONES. PART IV. SYNTHESIS AND ELECTROPHILEINDUCED CYCLIZATION REACTIONS OF 3-METHYL-1-METHYLSULFONYLPENTA-1,2,4-TRIENE

Published Sep 1, 2004 · V. Christov, Ivaylo K. Ivanov

Phosphorus, Sulfur, and Silicon and the Related Elements

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Abstract

A method for synthesis of 3-methyl-1-methylsulfonylpenta-1,2,4-triene (3) by [2,3] sigmatropic rearrangement of 3-methylpent-1-en-4-yn-3-yl methanesulfinate (2), formed in the reaction of 3-methylpent-1-en-4-yn-3-ol (1) with methylsulfinyl chloride has been found. Electrophile-induced reactions of the vinylallenyl sulfone (3) occur in different pathways depending on the used electrophiles. The halogenation leads to the formation of (1E)-2-halo-3-methylene-1-methylsulfonylpenta-1,4-dienes (4) and (5). Reactions with phenylsulfenyl and phenylselenenyl chlorides afford only heterocyclic products, 3-methyl-2-[methylsulfonylmethyl]thiophene (6) in the case of sulfenyl chloride, and a mixture of 2,5-dihydroselenophene (7) and selenophene (8) in the case of selenenyl chloride.

Study Snapshot

This study demonstrates a method for synthesizing 3-methyl-1-methylsulfonylpenta-1,2,4-triene by [2,3] sigmatropic rearrangement of 3-methylpent-1-en-4-yn-3-yl methanesulfinate,

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

ALKATRIENYL SULFOXIDES AND SULFONES. PART IV. SYNTHESIS AND ELECTROPHILEINDUCED CYCLIZATION REACTIONS OF 3-METHYL-1-METHYLSULFONYLPENTA-1,2,4-TRIENE

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References

Citations

Bifunctionalized Allenes. Part VIII. An Efficient and Varied Method for the Synthesis of 2-Sulfonylated Alka-2,3-Dienoates

This efficient method for synthesizing 2-sulfonylated alka-2,3-dienoates efficiently utilizes the high acidity of the hydrogen atom at the allenic C-1 atom and the [2,3]-sigmatropic rearrangement.

Bifunctionalized Allenes, Part IX: An Efficient Method for Regioselective Synthesis of 4-Heteroatom-Functionalized Allenecarboxylates

This efficient method allows for the synthesis of 4-heteroatom-functionalized allenecarboxylates, with potential applications in organic synthesis and catalysis.

Alkatrienyl Sulfoxides and Sulfones, VIII: Diels–Alder Reaction of 3‐Methylpenta‐1,2,4‐trienyl Phenyl Sulfoxide with Maleic Anhydride

The Diels-Alder reaction of 3-methylpenta-1,2,4-trienyl phenyl sulfoxide with maleic anhydride produces sulfinyl-substituted benzofuran or norbornene cycloadducts in

Alkatrienyl Sulfoxides and Sulfones. V. Tandem Cyclization, Rearrangement, and Aromatization of 1‐ and 3‐Vinylallenyl Sulfoxides and Sulfones in Diels‐Alder Reaction

The Diels-Alder reaction of 1 and 3vinylallenyl sulfoxides and sulones with dimethyl but-2-ynedioate leads to the formation of 4sulfinyl(sulfonyl) or 3

Synthesis and electrophilic cyclization reactions of diphenyl 3‐methylhexa‐ 1,3,4‐trien‐3‐yl phosphine oxide

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Selenophenes and their fused derivatives show potential for biologically active compounds and applications in various fields.

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Sigmatropic rearrangements of propargyl sulfonium ylides and related transformations have been studied in detail, offering new insights into the chemistry of propargylic and allenic systems.