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Table 2 Dehalogenation and regioselective demethoxylation of 1a–1c, 2a–2c and 3a–3c
figure b

From: Regioselective alkali metal reduction of dibenzocyclooctadiene lignan derivatives, demethoxylation followed by dehalogenation

Entrya

Substrate

Products (Convb, %)

1

1a

–

1 (2)

1′ (83)

2

1b

1b′ (5)

1 (10)

1′ (71)

3

1c

–

1 (35)

1′ (53)

4

2a

–

2 (16)

2′ (62)

5

2b

–

2 (26)

2′ (57)

6

2c

–

2 (37)

2′ (57)

7

3a

3 (20)

3′ (12)

3′′ (50)

8

3b

3 (23)

3′ (18)

3′′ (58)

9

3c

3 (24)

3′ (14)

3′ (62)

  1. aReaction was performed with substrate (0.0426 mmol), Na (100 eq), t-butanol (8 mL) at 50 °C until all of sodium was dissolved
  2. bConversions of the products were determined by HPLC with UV detection at 254 nm
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BMC Chemistry

ISSN: 2661-801X

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