Insect chemistry. Application of the norrish type-I reaction to the synthesis of propylure, the sexual pheromone of pectinophora gossypiella saunders.

Kossanyi, J.; Furth, Bernard; Morizur, J.-P.

doi:10.1016/s0040-4039(01)86942-2

Cited by 15 publications

(1 citation statement)

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“…2 This Norrish photo-chemistry has been extensively exploited in a wide range of experiments, including photoinitiated polymerization, and chemical synthesis. [3][4][5][6][7][8][9][10][11][12][13] It is also signicant in the photolysis of volatile carbonyl compounds such as acetone in the Earth's atmosphere. [14][15][16][17][18] The biradical intermediates formed by a-cleavage of a cyclic ketone can further react in several different ways, with pathways that depend on the ring size of the ketone.…”

Section: Introductionmentioning

confidence: 99%

Effects of ring-strain on the ultrafast photochemistry of cyclic ketones

et al. 2020

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Section: Introductionmentioning

confidence: 99%

Effects of ring-strain on the ultrafast photochemistry of cyclic ketones

et al. 2020

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The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Krapcho

Ciganek

2013

Organic Reactions

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The Krapcho reaction involves esters with α‐electron‐withdrawing substituents such as malonates, β‐keto esters, and α‐cyano esters, which undergo dealkoxycarbonylation on being heated in polar aprotic solvents (such as DMSO, DMF, or HMPT) in the presence of water, or in polar aprotic solvents with water in the presence of added salts (such as NaCN, NaCl, LiCl, LiI, or MgCl 2 ). This procedure avoids the use of strongly aqueous acidic and alkaline conditions and tolerates many functional and protecting groups. The chapter presents the mechanistic aspects of this procedure, which include reaction parameters such as solvents, salts, other additives, and the use of microwave irradiation. The diastereoselectivity of protonation of the enolate intermediate leading to the dealkoxycarbonylated products is discussed. Trapping of the intermediate enolate by electrophiles other than a proton is illustrated. Potential side reactions and same‐pot subsequent reactions of substrates are discussed along with functional‐group compatibility for halogens and nitrogen, oxygen, sulfur, selenium, and carbon functional groups. Several examples of applications of this methodology for the synthesis of natural products along with experimental conditions and procedures are presented. Closely related methods are discussed in the Comparison with Other Methods section. The tables, which consist of 371 pages, are grouped according to substrate structure. Selective entries for other methods (excluding classical aqueous acidic or basic methods) are included in the tabular survey for comparative purposes.

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