Premium
Synthesis of Functionalized Cyclooctynes as Building Blocks for Non‐covalent Surface‐Orthogonal Chemistry
Author(s) -
Scharf Dominik,
Jaschke Clara M.,
Ivlev Sergei,
Koert Ulrich
Publication year - 2025
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202500124
Abstract Cyclooctynes substituted with functional groups capable for hydrogen bonding (amide, imide, carboxylic acid) have been synthesized. The 8‐membered ring was derived from cyclooctadiene, by Beckmann rearrangement or by ring‐closing metathesis. The transannular instability of a monocyclic cyclooctyne lactam was postulated. Three stable functionalized cyclooctynes obtained are candidates for a surface‐orthogonal layer‐by‐layer synthesis on semiconductor surfaces (in particular the Si(001) surface).