Thiol–Ene (Click) Reactions as Efficient Tools for Terpene Modification

Abstract

This Focus Review highlights the application of thiol-ene (click) chemistry to the productiono fadiverse range of materials that are derived from terpenes. To present an overview concerning the potencyo ft erpenes as renewable resources, recent advances in their developmentb y using synthetic organic chemistry are initially discussed. In addition, the use of thiol-enec hemistry as an efficient approach and versatile tool for noncatalytic carbonÀheteroatom bond formation is briefly presented, including mecha-nistic and kinetic aspects, as well as some structuralc onsiderations,t hat is, the influenceo ft he thiol and olefin structures, which should be well-thought-out before applying such chemistry.T his discussiona lso coversh ow an initiator works and its effect on the reactionr ate. Moreover,t he utilization of thiol-ene reactions for the synthesis of terpenebased valuable platform chemicals, monomers, and polymers, includingr ecent examples that demonstrate its broad utility,a re highlighted.[a] Dr.M.F irdaus Scheme11. Terpene-basedp olythioethers thatwere prepared by thiol-ene photopolymerization. [100] Scheme12. Preparation of cross-linkedthin films that were derived from limonene and their possible addition type. [101] Asian

A role for terpenoid cyclization in the atom economical polymerization of terpenoids with sulfur to yield durable composites

“…The efficient formation of C-S bonds upon reaction of terpenes with sulfur radicals in the course of thiol-ene reactions has been established, 46,47 and a variety of terpenoids have been used as comonomers for reaction with sulfur by the inverse vulcanization pathway. 12,13 For the current study, it was thus hypothesized that terpenoid-sulfur composites ( Fig.…”

Synthesis and Characterisation of Copoly-(Eugenol-N,N′-Methylene Bis(Acrylamide))

“…There are various classes of bio-based monomers such as phenylpropane, terpene, steroid, fatty acid derivatives, etc. [7][8][9][10] One biobased starting material which has the potential to be utilised as a monomer is eugenol. 7,[11][12][13] Eugenol is an aromatic and/or phenolic compound which is the main volatile component of clove oil (ca.…”

From terpenes to sustainable and functional polymers

“…Their structural diversity (i.e., being linear, cyclic or polycyclic) and the presence of double bonds with different reactivity render terpenes as highly versatile and easy to functionalize building blocks. [70][71][72] Limonene, a commercial monoterpene that can be isolated from citrus fruits (Fig. 1), 73 represents a terpene structure that comprises of two distinct double bonds that can be easily modified, for instance by epoxidation or thiol-ene click reactions.…”