Β-scission Of Alkoxyl Radicals Research Articles

Photoinduced alkylation of pyrazolones via β-scission of unstrained aliphatic alcohol derivatives

An efficient radical approach was reported for the transformation of unstrained aliphatic alcohols through the β-scission of alkoxyl radicals.

ChemInform Abstract: Photoinduced Molecular Transformations. Part 121. New Short Step General Synthesis of Isobenzofuran-1(3H)-ones (Phthalides) Based on a Single or Double β-Scission of Alkoxyl Radicals Generated from 1- Ethylbenzocyclobuten-1-ols and fr

ChemInform Abstract: Photoinduced Molecular Transformations. Part 121. New Short Step General Synthesis of Isobenzofuran-1(3H)-ones (Phthalides) Based on a Single or Double β-Scission of Alkoxyl Radicals Generated from 1- Ethylbenzocyclobuten-1-ols and fr

ChemInform Abstract: Photoinduced Molecular Transformations. Part 131. Synthesis of 18- Norsteroids, Deoxofukujusonorone and the Related Steroids, Based on a Selective β-Scission of Alkoxyl Radicals as the Key Step.

A new transformation of steroids into 18-norsteroids under mild conditions is described. The key step was a regioselective β-scission of the alkoxyl radicals generated by photolysis of the hypoiodite of 18-hydroxy-18,20α-epoxy steroids, prepared by photolysis of steroidal 20α-ol nitrites followed by deoximation of the resulting 18-hydroxyimino-20α-hydroxy steroid with sodium nitrite and acetic acid. 3β-Hydroxypregn-5-en-20-one (pregnenolone) was thus transformed into 3β-hydroxy-18-norpregna-5,13-dien-20-one (12-deoxofukujusonorone) in 10 steps.

A new synthesis of a functionalized bicyclo[5.4.0]undecane skeleton based on a sequence involving [2 + 2] photoaddition and regioselective β-scission of alkoxyl radicals generated from the resulting cyclobutanols

A new general synthesis of a functionalized bicyclo[5.4.0]undecane skeleton based on a regioselective β-scission of the alkoxyl radicals generated from 2-hydroxytricyclo[5.4.0.02,6]undecan-8-ones (prepared by [2 + 2] photoaddition of cyclic enones with the trimethylsilyl enol ethers of cyclic ketones) is described.

Photoinduced molecular transformations. Part 112. Transformation of steroids into ring-A-aromatized steroids and 19-norsteroids involving a regioselective β-scission of alkoxyl radicals; synthesis of two marine natural products, 19-nor-5α-cholestan-3β-ol and 19-norcholest-4-en-3-one, and new synthesis of estrone and 19-nortestosterone

A new transformation of steroids into 19-norsteroids and ring-A-aromatized steroids is described. The transformation method involves the removal of the 10β-methyl group by a regioselective β-scission of alkoxyl radicals. Cholesterol was transformed into two marine natural products, 19-nor-5α-cholestan-3β-ol and 19-norcholest-4-en-3-one, and into 19-norcholesta-1,3,5(10)-trien-3-ol. Transformations of 3β-hydroxyandrost-5-en-17-one into 19-nortestosterone, estrone, and the related estranes are also described.