One‐pot Synthesis of 1,3‐Butadiene and 1,6‐Hexanediol Derivatives from Cyclopentadiene (CPD) via Tandem Olefin Metathesis Reactions

Turczel, Gábor; Kovács, E.; Csizmadia, Eszter; Nagy, Tibor; Tóth, Imre; Tuba, Róbert

doi:10.1002/cctc.201801088

Cited by 2 publications

(3 citation statements)

References 73 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1,6‐Diacetoxy‐2,4‐hexadiene ( 1 ) coeluted with Z ‐1,4‐diacetoxy‐2‐butene. 1 H NMR of 1 matches the literature [49,50] . 1 H NMR (500 MHz, Chloroform‐ d ) δ 6.28 (d, J =14.6 Hz, 1H), 5.80 (ddd, J =12.3, 9.7, 6.6 Hz, 2H), 4.60 (d, J =6.0 Hz, 2H), 2.07 (s, 6H).…”

Section: Methodssupporting

confidence: 81%

Degradation of Polyvinyl Chloride by Sequential Dehydrochlorination and Olefin Metathesis

Chang

Braslau

2023

ChemPlusChem

View full text Add to dashboard Cite

Polyvinyl chloride (PVC) is a problematic waste plastic with limited options for recycling or upcycling. Herein, we demonstrate preliminary results in breaking down the long carbon chains of PVC into oligomers and small organic molecules. First, treatment with a substoichiometric amount of alkali base effects elimination of HCl to form a salt and creates regions of conjugated carbon-carbon double bonds, as determined by 1 H NMR and UV-Vis spectroscopy. Olefin cross metathesis with an added partner alkene then cleaves carbon-carbon double bonds of the polymer backbone. Addition of allyl alcohol to the dehydrochlorination step introduces allyloxy groups by substitution of allylic chlorides. Subsequent metathesis of the pendant allyloxy groups provides a reactive terminal alkene to promote insertion of the metathesis catalyst onto the olefins in the all-carbon backbone. The products obtained are a mixture of PVC oligomers with greatly reduced molecular weights and a small-molecule diene corresponding to the substituents of the added alkene, as evidenced by 1 H and DOSY NMR and GPC. This mild procedure provides a proof of concept towards harvesting carbon resources from PVC waste.

show abstract

Section: Methodssupporting

confidence: 81%

Degradation of Polyvinyl Chloride by Sequential Dehydrochlorination and Olefin Metathesis

Chang

Braslau

2023

ChemPlusChem

View full text Add to dashboard Cite

show abstract

“…Although the yield of the metathesis reaction is low (11%), this reaction is highly relevant as it demonstrates the applicability of metathesis reactions in the synthesis of conjugated double bond systems. [44][45][46][47] Scheme 8. Synthesis of pheromone of Cydia pomonella (20)…”

Section: Scheme 7 Three Different Routes To E-9-decenyl-acetate (14) the Pheromone Of Platynota Stultanamentioning

confidence: 99%

“…The reaction of 2,4-hexadiene ( 18 ) with chloroolefin 17 provided the desired ( E , E )-diene intermediate 19 , which was then converted to pheromone 20 . Although the yield of the metathesis reaction is low (11%), this reaction is highly relevant because it demonstrates the applicability of metathesis reactions in the synthesis of conjugated double bond systems. − …”

Section: Pheromone Synthesis Via Cross-metathesismentioning

confidence: 99%

Synthesis of Semiochemicals via Olefin Metathesis

Turczel

Kovács

Merza

et al. 2018

ACS Sustainable Chem. Eng.

Self Cite

View full text Add to dashboard Cite

Semiochemicals are substances or mixtures that carry messages and are used for communication between individuals of the same or different species. Semiochemicals that are used in pest control are called biopesticides. Conventional pesticides, which are generally synthetically derived and unnatural, inactivate or kill the pests, whereas biopesticides are naturally occurring compounds that attract insects to a trap or interfere with their reproduction.There are several advantages to biopesticides. Compared to conventional pesticides, biochemical-based pesticides are often less toxic and therefore pose a significantly lower impact 2 on human health and the environment. Moreover, the biopesticides are pest selective and as such, do not negatively impact other organisms such as insects, mammals or birds. Other advantages of biopesticides include high potency, meaning that smaller amounts of biopesticide are required, less resistance by target organisms, and the ability to biodegrade more quickly than conventional pesticides. [1][2][3] Although the biochemical-based pesticides are very promising materials, their production is often cumbersome and their application is often limited. So far, most of the biopesticides are synthesized by multistep, classical organic reactions which are not economical and pose high environmental impact. However, in recent decades, many efforts have been done to implement cost-effective and safer chemical procedures for the widespread application of biochemical-based pesticides. The purpose of this perspective is to draw the attention of the green chemistry community to the applicability of olefin metathesis reactions in environmental benign and cost-effective biopesticide synthesis. In this article, we review seminal work on the total synthesis of biopesticides using olefin metathesis as a key reaction step, and in doing so, we hope to inspire new ideas for forthcoming olefin metathesis based biopesticide development.

show abstract

One‐pot Synthesis of 1,3‐Butadiene and 1,6‐Hexanediol Derivatives from Cyclopentadiene (CPD) via Tandem Olefin Metathesis Reactions

Cited by 2 publications

References 73 publications

Degradation of Polyvinyl Chloride by Sequential Dehydrochlorination and Olefin Metathesis

Degradation of Polyvinyl Chloride by Sequential Dehydrochlorination and Olefin Metathesis

Synthesis of Semiochemicals via Olefin Metathesis

Contact Info

Product

Resources

About