Alkoksyalleny : metody otrzymywania i zastosowanie w syntezie organicznej

• Autorzy: Łysek, R. , Chmielewski, M.

Warianty tytułu

EN

Alkoxyallenes : methods of preparation and application to organic synthesis

• Języki publikacji: PL

Abstrakty

EN

The present short review describes methods of preparation and synthetic applications of alkoxyallenes. The title compounds can be obtain by variety of methods based on elimination, substitution, addition, isomerization and alkylation reactions. Methods based on elimination reactions and on substitution of halogen, or alkoxy substituent in allenes, or propargyl derivatives are not of great importance. The most important method of preparation of alkoxyallenes is based on isomerisation of propargyl ethers. The rearrangement triple bond/allene offers possibility of introduction of alkyl or silyl substiuents by consecutive deprotonation-alkylation and/or silylation steps. Alkoxyallenes undergo readily deprotonation a to the alkoxy group by treatment with n-butyl lithium. The resulting lithium salt reacts with electrophiles such as carbonyl compounds and alkyl halides to afford substituted alkoxyallenes. Subsequent hydrolysis of alkoxyallene fragment provides a,b-unsaturated carbonyl compounds. 1-Alkoxy-1-hydroxyalkylallenes in the presence of strong bases gave alkoxydihydrofurans or tetrahydrofuranones. Alkoxyallenes subjected to [4+2]-, [2+2]-, and (1,3)-dipolar cycloaddition afford variety of heterocyclic compounds. Five- and six-membered heterocycles having exo-double bond may undergo rearrangements to form more stable compounds. Attractive chemical properties prompted many laboratories to use alkoxyallenes for the synthesis of natural products. Syntheses of (+)-goniodiol 58, methylenomycin B 71, erigerol 89, (+)-allopumilitoxin 267 A 91, lacramin A 158, cytochalastin B 159 and (š)-xanthocidin 162 are the most representative. Alkoxyallenes undergo radical, cationic and coordination polymerization providing polymers having exo-methylene groups. In certain cases, alkoxyallenes may undergo spontaneous polymerization or polyaddition.

Słowa kluczowe

PL

alkoksyalleny; synteza alkoksyallenów

EN

alkokxyallenes; organic synthesis

• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2001
• Tom: [Z] 55, 7-8
• Strony: 657-691
• Opis fizyczny: schem., bibliogr. 101 poz.

Twórcy

autor

Łysek, R.

• Instytut Chemii Organicznej Polskiej Akademii Nauk ul. M. Kasprzaka 44/52,01-224 Warszawa

autor

Chmielewski, M.

• Instytut Chemii Organicznej Polskiej Akademii Nauk ul. M. Kasprzaka 44/52,01-224 Warszawa

• Instytut Chemii Organicznej Polskiej Akademii Nauk, ul. M.Kasprzaka 44/52, 01-224 Warszawa

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Uwagi

PL

Opracowane ze środków MEiN, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2022-2023).