By Malcolm Sainsbury
Hardbound. numerous vitally important parts of fragrant chemistry are spanned during this quantity. It contains chapters dedicated to benzoquinones, nitro compounds, metallo derivatives and fragrant hydrocarbons with substituents which include multiple nitrogen atom, e.g., azobenzenes, azides, and so on.
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Extra resources for Chemistry of Carbon Compounds: 2nd Supplement to 2r.e v.3B, C, D
Appl. Environ. , 1992, 5_88,221), and in the iron(Ill) catalysed oxidative degradation of 4-substituted-l,2-dimethoxybenzenes (veratroles): electronaccepting substituents such as formyl and acetyl induce the formation of muconic acids, whereas donor substituents such as tbutyl and hydroxymethyl lead to the formation of 5-substituted-2methoxy-l,4-benzoquinones (1. Artaud, K. Ben-Aziza and D. Mansuy, J. Org. _88,3373). Although 1,2- and 1,4-benzoquinones can be destroyed by oxidation, a route favoured in Nature involves reduction to the corresponding hydroquinones followed by oxygenation prior to ringcleavage (cf.
Kim and L. von dem Bussche, J. Org. , 1994, 59, 3248). The formation of 1,2-benzoquinone monomethides from benzo[b]thiete (111) and the bisthiete (112) has been noted in Section 5(b). The imine (124) has also been prepared (L. Field and C. Lee, J. Org. , 1990, 55, 2558). W. , J. Org. 5, 4039); they behave as heterodienes in DielsAlder reactions with alkenes (G. Desimoni, G. P. W. , J. Org. , 1989, 5_44,5926). In these instances the quinonoid moiety becomes benzenoid, providing the driving force (cf___,1,2.
Chem. , Chem. , 1978, 397; D. , J. Org. , 1985, 50, 1853; J. S. K. Snyder, J. Org. , 1990, 55, 5013). Addition of the diene to monoalkyl-l,2-benzoquinones occurs at the least-substituted enone moiety (S. Knapp and S. Sharma, J. Org. , 1985, 50, 4996). L. M. Weinreb, "Hetero-Diels-Alder Methodology in Organic Synthesis", Academic Press, San Diego, 1987, pp. -L. Ho, "Polarity Control for Synthesis", Wiley, New York, 1991, pp 224-231), especially via inverse electron-demand. Thus, 4-t-butyl-1,2-benzoquinone reacts readily with the enamine (52) to afford the dihydrodioxin (53) (Y.