Short-lived intermediates. 6. Cyclization of the 1,4-diradical in ester photochemistry. Completion of an analogy found wanting

Marron, Neil A.; Gano, James E.

doi:10.1021/ja00431a057

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1976

2010

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“…decarboxylation by irradiation of the diester(29) in methanol provides an ingenious route to [2,2]paracyclophane(30) in yields of up to 70% .30 Kaupp3' has observed three new examples of [6 + 61 photocleavage of [2,2]cyclophanes, including the formation of the tetraene (31) on irradiation of the cyclophane (30) at low temperatures.…”

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Chapter 8. Photochemistry

Carless¹

1976

Annu. Rep. Prog. Chem., Sect. B

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confidence: 99%

Chapter 8. Photochemistry

Carless¹

1976

Annu. Rep. Prog. Chem., Sect. B

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Baeyer‐Villiger Oxidation

2010

Comprehensive Organic Name Reactions and Reagents

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Oxidation of ketones or cyclic ketones into esters or lactones by peracids or hydrogen peroxide is known as the Baeyer–Villiger oxidation. Some of the typical peracids have been found to involve in this type of the reaction are peroxybenzoic acid, m ‐chloroperoxybenzoic acid ( m CPBA), peroxyacetic acid, and trifluoroperoxyacetic acid. In this reaction the substituted group often migrates in the following order: tertiary > secondary > cyclohexyl > benzyl >phenyl > primary > methyl and stereochemistry and chirality of the migrating group are retained during the reaction. This reaction has wide application in the synthesis of esters and lactones.This reaction has been extensively reviewed and modified using bis[trimethylsilyl]peroxide or basic hydrogen peroxide.

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