A Convenient Method for the Synthesis of Insect Growth Regulators Cyclopentene Analogs of Alkyl (2<i>E</i>,4<i>E</i>)‐Dodecadienoates

Novák, Lajos; Rohaly, J.; Gálik, György; Fekete, Jenő; Varjas, L.; Szántay, Csaba

doi:10.1002/jlac.198619860309

Cited by 5 publications

(1 citation statement)

References 21 publications

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“…Novak and co-workers 69 have published the preparation of other cyclopentenyl derivatives. They carried out activity tests on two different insect species (Pieris brassicae and SarcoplJaga bullata) and compared their activity with that of methoprene (XIX) and hydroprene (XXVI) on the same insect species.…”

Section: Aliphatic Luvenoidsmentioning

confidence: 99%

Insect juvenile hormones and their bioanalogues

Wimmer

Romaňuk

1989

Collect. Czech. Chem. Commun.

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This survey supplements and up-dates review articles of other authors published in the field of substances affecting the development of the insect, juvenoids. Attention has been paid primarily to such structures as deserved more detailed investigation in the given field owing to their biological properties, further to less known structures and facts, and lastly to the most recent information from literature, mainly paying attention to the present trend in searching for structural types of substances affecting insect development. The synthetic juvenoids discussed are divided into chapters, on the basis of the skeleton of the molecule, on aliphatic juvenoids, juvenoids with one aromatic ring in the molecule and finally juvenoids with two and more cycles (aromatic as well as non-aromatic) in the molecule. Certain attention has also been paid to optically active juvenoids. Finally the role is mentioned of complex hormonogen compounds, juvenogens, in the protection of cultured plants against economically important insect pests.

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Section: Aliphatic Luvenoidsmentioning

confidence: 99%

Insect juvenile hormones and their bioanalogues

Wimmer

Romaňuk

1989

Collect. Czech. Chem. Commun.

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The Catalyzed NucleophilicAddition of Aldehydes to Electrophilic Double Bonds

1991

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The cyanide‐ion‐catalyzed dimerization of aromatic and heterocyclic aldehydes to α‐hydroxy ketones, also known as the benzoin condensation, is one of the oldest reactions in organic chemistry. A key intermediate in this reversible reaction is a nitrile‐stabilized carbanion. In 1973 it was shown that these carbanions add irreversibly to α,β‐unsaturated ketones, esters, and nitriles to give 1,4‐diketones, 4‐ketocarboxylic esters, and 4‐ketocarbonitriles, respectively. The reaction succeeds only in aprotic solvents, preferably dimethylformamide. Benzoins and aldehydes can be used interchangeably as starting materials since they are in rapid equilibrium. Cyanide ion catalysis fails with aliphatic aldehydes because they resinify under the strongly basic conditions. Vitamin B 1 (thiamine) has long been known to convert aliphatic aldehydes into acyloins in buffered aqueous solution. The catalytic effect of vitamin B 1 is due to the presence of a thiazolium cation. Thiazolium salts in general as well as other azolium salts also catalyze the formation of acyloins. The optimum conditions for thiazolium salt catalysis have been worked out. It was shown subsequently that thiazolium salts, in combination with bases, also catalyze the addition of aliphatic, aromatic, and heterocyclic aldehydes to α,β‐unsaturated carbonyl compounds. The 1,4‐diketones, 4‐ketocarboxylic esters, and 4‐ketocarbonitriles are usually formed in good to excellent yields. Cyanide ion and thiazolium salt catalysis thus complement each other. This chapter covers the literature of the catalyzed nucleophilic addition of aldehydes to electrophilic double bonds up to 1988. The reaction has been reviewed previously.

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