Download PDF by Guenter Grethe: Isoquinolines, Part 1 (The Chemistry of Heterocyclic

By Guenter Grethe

ISBN-10: 0471374814

ISBN-13: 9780471374817

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Extra info for Isoquinolines, Part 1 (The Chemistry of Heterocyclic Compounds, Volume 38)

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HYPERFINE CONSTANTS QUINOLINE ~~ SPLITTING FOR ISO- ~ ~ Experimental Position Ref 98 Ref. 13). A striking similarity was noted between the uv spectra of the radical ions produced from naphthalene, quinoline, and isoquinoline, but with the absorption maxima of the aza compounds moved t o shorter wavelength. The radicals produced when isoquinoline or 3-methylisoquinoline are irradiated at low temperature are formed"" by a monophotonic process. Spin densities of radicals 54 and their theoretical second moments ( M 2 ) have been calculated and the values 111.

Yield by the reaction between isoquinoline and dimsyl sodium. 2-Acyl and 39 1V. Reactions CH,CN 117 CN 118 119 2-arylsulfonyl quaternary salts react easily with a variety o f nucleophiles at C-1. When cyanide ion is used, the products 120 are the Reissert com- dN 120 R = COPh o r SO& The nucleophilic displacement of substituents such as hydroxyl or halogen attached to C-1 or C-3 is a commonly observed reaction and is unexceptional. ) in the presence of sodium amide. A similar sequence has been applied'X3 t o 1-chloroisoquinoline t o yield 121.

The same technique has been applied to 1-is~quinolinol,'~"and the order of exchange in 61"/0 D,SO, was found to be 3 > 5 b 7 > 8 > 3. The exclusive attack of nucleophiles and radicals at C-1 in both isoquinoline and its quaternized form is successfully predicted from the appropriate localization energies; this forms the basis of the most successful 32 Properties and Reactions of Isoquinolines approach127 to relative site reactivities in isoquinolines, although other reactivity indices are sometimes employed with certain specific reasons, for example, the use of superdelocalizability in the case of the oxidative cyanation of isoquinoline N - 0 ~ i d e .

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Isoquinolines, Part 1 (The Chemistry of Heterocyclic Compounds, Volume 38) by Guenter Grethe


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