Thermal acid-catalysed rearrangements of natural chrysanthemic acids

Otieno, Dismas A.; Pattenden, Gerald; Popplestone, C. R.

doi:10.1039/p19770000196

Cited by 11 publications

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“…The published IR and 1 H NMR spectroscopic data for this compound 8j do not, however, fit an enol lactone structure such as the model lactone 8n (Figure 2), also found in the literature 18. Compounds 7j and 8j displayed similar IR absorptions [ 7j : 1718 (C=O acetate) and 1685 cm –1 (C=O ketone); 8j : 1722 cm –1 ], whereas the enol lactone 8n showed an absorption at 1755 cm –1 .…”

Section: Resultsmentioning

confidence: 99%

Epoxidation of 4‐Alkylidenecyclopentenones: A Route to the 1‐Oxaspiro[2.4]hept‐6‐en‐5‐one Framework

2012

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Section: Resultsmentioning

confidence: 99%

Epoxidation of 4‐Alkylidenecyclopentenones: A Route to the 1‐Oxaspiro[2.4]hept‐6‐en‐5‐one Framework

2012

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“…214 It has been also reported that reaction of trans-chrysanthemic acid trans-1aH with pyridinium hydrochloride, carried out at 220 °C, leads to a series of compounds resulting from the cyclopropane ring opening in 77% overall yield (Scheme 150). 352 The dienoic acid L-117aH, possesses the lavandulyl skeleton (Scheme 144) and results from the [Cc−Cd] bond cleavage, and the diene 118 from a retroaldol reaction. 352 The five membered-S-113, A-120 and six-membered-L-119, A-120, L-121 lactones formation that includes pyrocine S-113, results from the effect of the high temperature on the different product resulting from the cyclopropane ring fission.…”

Section: Cyclopropane Ring Opening Under Thermal Conditionsmentioning

confidence: 99%

“…352 The dienoic acid L-117aH, possesses the lavandulyl skeleton (Scheme 144) and results from the [Cc−Cd] bond cleavage, and the diene 118 from a retroaldol reaction. 352 The five membered-S-113, A-120 and six-membered-L-119, A-120, L-121 lactones formation that includes pyrocine S-113, results from the effect of the high temperature on the different product resulting from the cyclopropane ring fission. 352 Scheme 150.…”

Section: Cyclopropane Ring Opening Under Thermal Conditionsmentioning

confidence: 99%

“…352 The five membered-S-113, A-120 and six-membered-L-119, A-120, L-121 lactones formation that includes pyrocine S-113, results from the effect of the high temperature on the different product resulting from the cyclopropane ring fission. 352 Scheme 150. Compounds generated from the reaction at 220 °C of trans-chrysanthemic acid with pyridinium hydrochloride.…”

Section: Cyclopropane Ring Opening Under Thermal Conditionsmentioning

confidence: 99%

“…352 Alkyl chrysanthemates 1aR also react with different protic acids and among others sulfuric acid in a two phase system (hexane/water; Scheme 151, entries a-d), 90 p-toluenesulfonic acid in toluene (PTSA; Scheme 151, entry e), 152 or methanesulfonic acid in 1,2-dichloroethane (Scheme 151, entries f,g). 338,351 They deliver under conditions (70-110 °C; Scheme 151, entries a-c, e-g) 90,152,338,351 that are less drastic than those disclosed in Scheme 150, 352 mainly products possessing the lavandulyl (L)-skeleton (Scheme 144) that result from the [Cc−Cd] bond cleavage of their cyclopropane ring (Scheme 151, route b). Rising the temperature up to 130 °C drastically lowers the amount of the open chain products at the advantage of lactone derivatives (structure not disclosed).…”

Section: Cyclopropane Ring Opening Under Thermal Conditionsmentioning

confidence: 99%

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Pyrethroid insecticides Chapter IVa. Reactivity of chrysanthemic acid and its lower esters

Krief¹

2022

Arkivoc

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The reactivity of chrysanthemic acid and of its "lower esters" (methyl, ethyl, isopropyl and t-butyl) has played a crucial role in their structure elucidation, the discovery of new insecticides and in the understanding of their environmental fate.The reactivity of the carboxylic acid moiety and of its esters, that of the isobutenyl moiety and that of the cyclopropane ring are orthogonal to each other. The fact that this compound class is of relevance for industry has increased the diversity of the reactions disclosed especially that in the patented literature that associates science and economy and is at the roots of the green chemistry.

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The Retro–Diels–Alder Reaction PartI.CCDienophiles

Rickborn

1998

Organic Reactions

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The Diels–Alder (“DA”) reaction is so familiar to organic chemists that the retro‐Diels–Alder or retro‐diene reaction (hereafter “rDA”) requires no conceptual introduction. However, a working definition is needed to indicate the coverage of this review. The intent is to include all reported examples of the general skeletal process excluded in this chapter. Any of the atoms in the starting material (cycloadduct) may be carbon or heteroatom, and substituents on all positions are allowed. In addition, any bond order available to the element in any oxidation state is included, as well as bonding to non‐nearest neighbor atoms (bicyclics, etc.). The volume of literature required separation of this review into two parts. Part I covers all expelled C–C dienophiles, i.e. those reactions that generate a new carbon‐carbon double or triple bond in the dienophile that is formed. Part II, to appear later, covers those expelled dienophiles in which one or both atoms is a heteroatom. Certain specific topics are intentionally omitted. These are: rDA reactions invoked under mass spectral conditions; rDA reactions of polymeric substrates; Electrocyclic processes, some of which are arguably very similar to rDA reactions (these are not addressed unless needed for clarification of an rDA sequence); and a thorough discussion of homo‐rDA reactions. CAS‐Online searches resulted in ca. 1,300 references, of which ca. 900 proved pertinent to the rDA topic as defined and delimited above. Active literature searching was halted in April 1995, but occasional more recent articles are included. Over 2,500 pertinent references were eventually found. Most were obtained by perusal of primary literature (articles) and secondary sources (books and reviews). Computer based search success was limited mainly by the failure of authors or abstractors to key‐word this topic, an especially common occurrence when the expelled dienophile was a simple substance such as N 2 or CO 2 . Overall, approximately 3,500 books, chapters, reviews, articles, and abstracts were consulted in an effort to make this review as comprehensive as possible. This was done with the certainty that some pertinent literature would be missed, tempered by the view that these omissions are probably also lost to any future rational search method. Many secondary sources proved valuable not only for in‐depth discussion of certain rDA reaction types, but also for providing comparisons with related topics. To assist the reader, these secondary sources are referenced (alphabetically by first author within broad subject areas) with a title or brief note on the topic(s) addressed. The first group lists earlier reviews with primary focus on rDA reactions, followed by items of Historical/General Interest, reviews that deal with Experimental Methods, DA reactions (general and specific), reviews of Related Topics (these impinge in more or less significant ways on rDA reactions), and general treatments of Theory and Mechanism.

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Thermal acid-catalysed rearrangements of natural chrysanthemic acids

Cited by 11 publications

References 0 publications

Epoxidation of 4‐Alkylidenecyclopentenones: A Route to the 1‐Oxaspiro[2.4]hept‐6‐en‐5‐one Framework

Epoxidation of 4‐Alkylidenecyclopentenones: A Route to the 1‐Oxaspiro[2.4]hept‐6‐en‐5‐one Framework

Pyrethroid insecticides Chapter IVa. Reactivity of chrysanthemic acid and its lower esters

The Retro–Diels–Alder Reaction PartI.CCDienophiles

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