1-Bromo-2-ethoxycyclopropyllithium: A Synthetic Equivalent of 2-Lithio-or 3-Lithiopropenal. Application to the Synthesis of Juvenile Hormone (JH-II), β-Sinensal, and …

Y Morizawa, A Kanakura, H Yamamoto…

Index: Morizawa, Yoshitomi; Kanakura, Akihiro; Yamamoto, Hajime; Hiyama, Tamejiro; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 7 p. 1935 - 1942

Full Text: HTML

Citation Number: 21

Abstract

The ethyl vinyl ether-dibromocarbene adduct was lithiated with butyllithium at− 95° C in tetrahydrofuran. The resulting lithium carbenoid 3 was allowed to react with various electrophiles to give 1-substituted trans-1-bromo-2-ethoxycyclopropanes (1) in good yields. The trans relationship of Br and OEt groups was found particularly pertinent to the ethanolysis of 1 producing 2-substituted propenal diethyl acetal derivatives. The reaction ...

Related Articles:

Synthesis of 2-alkyl-2-cyclopenten-1-ones. A versatile kinetic alkylation-ozonolysis procedure for the preparation of γ-ketoaldehydes

[Geraghty, Niall W. A.; Morris, Noreen M. Synthesis, 1989 , # 8 p. 603 - 607]

Synthesis of 2-alkyl-2-cyclopenten-1-ones. A versatile kinetic alkylation-ozonolysis procedure for the preparation of γ-ketoaldehydes

[Geraghty, Niall W. A.; Morris, Noreen M. Synthesis, 1989 , # 8 p. 603 - 607]

Convenient synthesis of jasmonoid compounds from. gamma.-(trimethylsiloxy) butyronitrile

[Matsuda, Isamu; Murata, Shizuaki; Izumi, Yusuke Journal of Organic Chemistry, 1980 , vol. 45, # 2 p. 237 - 240]

Synthesis of 2-alkyl-2-cyclopenten-1-ones. A versatile kinetic alkylation-ozonolysis procedure for the preparation of γ-ketoaldehydes

[Geraghty, Niall W. A.; Morris, Noreen M. Synthesis, 1989 , # 8 p. 603 - 607]

2-(2-Nitroethyl)-1, 3-dioxolane as reagent for 3-oxopropyl anion synthon: a new route to jasmonoid and prostaglandin intermediates

[Rosini, Goffredo; Ballini, Roberto; Petrini, Marino; Sorrenti, Pietro Tetrahedron, 1984 , vol. 40, # 19 p. 3809 - 3814]

More Articles...