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1 article(s) from De Leger, Wout

Synthesis and post-functionalization of alternate-linked-meta-para-[2ⁿ.1ⁿ]thiacyclophanes

Wout De Leger,
Koen Adriaensen,
Koen Robeyns,
Luc Van Meervelt,
Joice Thomas,
Björn Meijers,
Mario Smet and
Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 2190–2197, doi:10.3762/bjoc.14.192

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Scheme 1: Macrocyclization towards homothiacalixarenes 3a and 3b [12].

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Scheme 2: Cyclocondensation reaction of 4 and 5 towards [2 + 2] and [3 + 3] adducts.

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Figure 1: X-ray crystal structure of alternate-linked-meta-para-thiacyclophane 6: (a) ball-and-stick represen...

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Scheme 3: Proposed reaction mechanism towards alternate-linked-meta-para-thiacyclophanes.

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Scheme 4: Attempted cyclocondensation with anisole derivative 13, products 14 and 15 were not formed.

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Scheme 5: Macrocyclization under acidic conditions, with only traces of 6 and 7 observed.

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Scheme 6: Post-functionalization of thiacyclophanes 6 and 7 with ethyl bromoacetate (17).

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Scheme 7: Modification of the functionalized [2 + 2] adduct 18 towards an amide derivative 20 and acid deriva...

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Published 22 Aug 2018

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Synthesis and post-functionalization of alternate-linked-meta-para-[2n.1n]thiacyclophanes

Synthesis and post-functionalization of alternate-linked-meta-para-[2ⁿ.1ⁿ]thiacyclophanes