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. 2021 Nov 1;22(21):11856. doi: 10.3390/ijms222111856

Table 10.

Preparation of aromatics by base-catalyzed dehydration of acrylonitrile-derived oxanorbornenes.

graphic file with name ijms-22-11856-i049.jpg

№ Oxanorbornene Yield of DA Adducts 1 Yield of Aromatic Products 1
1 R = dioxolane acetal 76 (ortho/meta ~1:1) 2 84 (ortho/meta ~1:1.5)
2 R = dioxolane acetal 76 (ortho/meta ~1:1) 86 (ortho/meta ~1:1.8) 3
3 R = Me 53 (ortho), 13 (meta) 97 (ortho), 62 (meta) 4
4 R = CH2OEt 36 (ortho), 18 (meta) 94 (ortho), 100 (meta) 4
5 R = CH2OH 47 (ortho), 26 (meta) 21 (ortho), 42 (meta) 4

1 Data were obtained from reference [31]. 2 After 120 h of the reaction. 3 CH3ONa as a base. 4 Relative to the corresponding ortho- or meta-DA cycloadduct.