Nickel‐Catalyzed, Geminal Dimethylation of Allylic Dithioacetals: (E)‐1‐Phenyl‐3,3‐Dimethyl‐1‐Butene

Yuan, Tzu-Hsuen; Luh, Tien‐Yau

doi:10.1002/0471264180.os074.20

Organic Syntheses 2003

DOI: 10.1002/0471264180.os074.20

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Nickel‐Catalyzed, Geminal Dimethylation of Allylic Dithioacetals: (E)‐1‐Phenyl‐3,3‐Dimethyl‐1‐Butene

Tzu-Hsuen Yuan

Tien‐Yau Luh

Abstract: Nickel‐catalyzed, geminal dimethylation of allylic dithioacetals: (E)‐1‐phenyl‐3,3‐dimethyl‐1‐butene intermediate: (E)‐2‐methyl‐2‐(2‐phenylethenyl)‐1,3‐dithiolane product: (E)‐1‐phenyl‐3,3‐dimethyl‐1‐butene

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2017

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Mass Efficiency of Alkene Syntheses with Tri- and Tetrasubstituted Double Bonds

Eissen

Lenoir

2017

ACS Sustainable Chem. Eng.

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Environmental factors and process mass intensity were determined and evaluated for more than 30 standard procedures for the synthesis of alkenes with tri- and tetrasubstituted double bonds. They contain some of the most commonly used reaction types for the synthesis of alkenes, e.g., Peterson, Shapiro, Heck, Suzuki, and Negishi. Four kinds of syntheses of geminal dihalides were also considered. The highest efficiency is found when employing the olefin metathesis reaction followed by other modern catalytic processes, and the lowest efficiency is found with the Julia–Lythgoe process. Several types of McMurry coupling reactions show that the efficiency is dependent on the variant of this type of reaction. These metrics point out weaknesses as well as optimization potentials and show which performances can be expected. This could provide an orientation when mass efficiency aspects are relevant during the synthesis planning of alkenes with tri- and tetrasubstituted double bonds.

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Mass Efficiency of Alkene Syntheses with Tri- and Tetrasubstituted Double Bonds

Eissen

Lenoir

2017

ACS Sustainable Chem. Eng.

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show abstract

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Nickel‐Catalyzed, Geminal Dimethylation of Allylic Dithioacetals: (E)‐1‐Phenyl‐3,3‐Dimethyl‐1‐Butene

Abstract: Nickel‐catalyzed, geminal dimethylation of allylic dithioacetals: (E)‐1‐phenyl‐3,3‐dimethyl‐1‐butene intermediate: (E)‐2‐methyl‐2‐(2‐phenylethenyl)‐1,3‐dithiolane product: (E)‐1‐phenyl‐3,3‐dimethyl‐1‐butene

Cited by 1 publication

References 18 publications

Mass Efficiency of Alkene Syntheses with Tri- and Tetrasubstituted Double Bonds

Mass Efficiency of Alkene Syntheses with Tri- and Tetrasubstituted Double Bonds

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