Phenylnitroso compound

Arylnitroso compounds of various types react with both electron-rich and electron-deficient dienes under mild conditions (usually 0-l(X)°C) to produce dihydrooxazines. As mentioned in the preceding section, Kresze s group has looked in considerable detail at orientational preferences and kinetics of [4 + 2] cycloadditions with various phenylnitroso compounds and substituted 1,3-dienes. Table 3-1 contains some of the results of cycloadditions of aromatic nitroso dienophiles with representative unsymmetrical 1- and 2-substituted dienes." Scheme 3-1 shows the subtle regiochemical trends that can be observed in a series of these reactions. These results were rationalized based on consideration of putative dipolar and nonpolar transition states and their relative stabilization by aromatic electron-donating and -withdrawing substituent groups. 

Phenylbutadiene, 80 Phenylmagnesium bromide, 23-27 Phenylnitroso compound, 72 Phenylsulfinyl chloride, 31... 

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See also in sourсe #XX -- [ ]

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