A reinvestigation of the reaction of .alpha.-pinene with hypochlorous acid

Wolinsky, Joseph; Vogel, Martin K.

doi:10.1021/jo00422a017

Cited by 9 publications

(3 citation statements)

References 11 publications

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“…Both HOCl and Cl 2 are strong oxidants and potentially react with many indoor chemicals. The reaction of HOCl with unsaturated species has been studied in the field of water disinfection and biochemistry. , It is known that HOCl reacts with unsaturated organic compounds by addition across the carbon–carbon double bonds forming chlorohydrins in the aqueous phase. , For example, it was found that terpene chlorohyrins were formed from the reaction of limonene with HOCl during citrus oil production . However, the reactivity of gaseous HOCl and Cl 2 in indoor air and on surfaces has only one report in the literature.…”

Section: Introductionmentioning

confidence: 99%

“…4,5 It is known that HOCl reacts with unsaturated organic compounds by addition across the carbon−carbon double bonds forming chlorohydrins in the aqueous phase. 6,7 For example, it was found that terpene chlorohyrins were formed from the reaction of limonene with HOCl during citrus oil production. 8 However, the reactivity of gaseous HOCl and Cl 2 in indoor air and on surfaces has only one report in the literature.…”

Section: Introductionmentioning

confidence: 99%

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Indoor Illumination of Terpenes and Bleach Emissions Leads to Particle Formation and Growth

Wang

Collins

Abbatt

2019

Environ. Sci. Technol.

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Application of chlorine bleach solution (major component sodium hypochlorite, NaOCl) in indoor environments leads to the emission of gaseous hypochlorous acid (HOCl) and chlorine (Cl2), both of which are strong oxidants. In contrast to the outdoor atmosphere, where mixing ratios of HOCl and Cl2 tend to be low (10s–100s of ppt), indoor HOCl and Cl2 can reach high levels during cleaning activities (100s of ppb or higher). HOCl and Cl2 may react with unsaturated organic compounds on indoor surfaces and in indoor air. In this study, we studied the reaction of limonene, one of the most common indoor volatile organic compounds (VOCs) arising from use of cleaning products, fragrance, and air fresheners, with HOCl and Cl2 in an environmental chamber. A dark reaction was observed between limonene and HOCl/Cl2 leading to gas-phase reaction products that were investigated using proton transfer reaction mass spectrometry (PTR-MS). With subsequent exposure to indoor fluorescent lights or diffuse sunlight through a nearby window, a substantial mass loading of secondary particles were formed with an averaged mass yield of 40% relative to the amount of limonene consumed. Aerosol mass spectrometry (AMS) measurements indicate a large contribution of particulate chlorine species. Electrospray ionization mass spectrometry (ESI-MS) analysis of filter-collected particles indicates the formation of high molecular weight products. This is the first study of the oxidation of limonene with HOCl and Cl2, and it illustrates the potential for particle formation to occur with indoor lighting during the use of common cleaning products.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Indoor Illumination of Terpenes and Bleach Emissions Leads to Particle Formation and Growth

Wang

Collins

Abbatt

2019

Environ. Sci. Technol.

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“…The keto-aldehyde 3, intermediate in the Wolinsky approach has also been used in the study of asymmetric cyclizations 12 and chemoselective reduction 13 . Only two other papers reported the formation of ketone 4: First, in 1977, Wolinsky 14 reported the formation of ketone 4 from α-Pinene (Fig. 2) and then, in 1996, Jones and Kover 15 demonstrated the formation of the enantiomer of ketone 4 by hydrolysis of epoxy-tosylates prepared from (-)-R-Carvone (Fig.…”

Section: Introductionmentioning

confidence: 99%

A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis

Castro¹,

Kover²,

Kover³

et al. 1999

J. Braz. Chem. Soc.

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Neste artigo apresentamos a oxidação direta do epóxi-limoneno 1 com KIO4 em água como uma melhor alternativa para se obter o ceto-aldeído 3, um importante intermediário na síntese de produtos naturais. O ceto-aldeído 3 é ciclizado com Al2O3-ácido de forma quimosseletiva produzindo, preferencialmente, a cetona 4. Estas duas reações elevam o rendimento total da síntese da cetona 4 para 70% em comparação com 8% pelo método citado na literatura 1 . This article presents the direct oxidation of limonene-oxide 1 with KIO4 in water, which is the best way to obtain the keto-aldehyde 3, an important intermediate in natural product synthesis. The cyclization of keto-aldehyde 3 with acidic Al2O3 proceeds chemoselectively to give ketone 4. These two reactions together increase the overall yield of ketone 4 to about 70% compared to 8% previously reported in the literature 1 .

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ChemInform Abstract: A REINVESTIGATION OF THE REACTION OF α‐PINENE WITH HYPOCHLOROUS ACID

Wolinsky¹,

Vogel²

1977

Chemischer Informationsdienst

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A reinvestigation of the reaction of .alpha.-pinene with hypochlorous acid

Cited by 9 publications

References 11 publications

Indoor Illumination of Terpenes and Bleach Emissions Leads to Particle Formation and Growth

Indoor Illumination of Terpenes and Bleach Emissions Leads to Particle Formation and Growth

A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis

ChemInform Abstract: A REINVESTIGATION OF THE REACTION OF α‐PINENE WITH HYPOCHLOROUS ACID

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