Table 1 Summary of calculated vs experimental selectivities of the reaction between anthracenes 1a–e and DMAD (D).

From: Diels–Alder reactions and electrophilic substitutions with atypical regioselectivity enable functionalization of terminal rings of anthracene

entry

anthracene

ΔΔG≠9,10–1,4 [kcal/mol]

calculated selectivity 9,10: 1,4

experimental selectivity 9,10: 1,4

1

1a

−6.2

9,10 only

>99: 1

2

1b

−1.4

10: 1

9: 1

3

1c

0

1: 1

1: 2.5

4

1d

1.5

1: 13

<1: 99

5

1e

6

1,4 only

<1: 99

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