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Highly Strained Unsaturated Carbocycles
Author(s) -
Zanda Matteo,
Bucci Raffaella,
Sloan Nikki L.,
Topping Lydia
Publication year - 2020
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.202000512
Subject(s) - bioorthogonal chemistry , chemistry , reactivity (psychology) , cycloaddition , ring strain , alkyne , ring (chemistry) , organic chemistry , click chemistry , catalysis , medicine , alternative medicine , pathology
Highly strained unsaturated carbocyclic rings are high‐energy compounds which are attracting increasing interest – not just for their peculiar structural and reactivity features – but also as modern chemical tools for bioorthogonal and in vivo chemistry, especially via inverse‐electron demand Diels–Alder (iEDDA) and strain‐promoted azide‐alkyne cycloaddition (SPAAC) reactions. This mini‐review covers two main classes of compounds: 3 to 10 membered‐ring cycloalkynes and trans ‐cycloalkenes, including some examples of cyclic enynes, dienes and bridgehead alkenes. Their molecular properties, synthesis and reactivity are presented and discussed, with an emphasis on their functionalization and reactivity.