A proposed sustainability index for synthesis plans based on input provenance and output fate: application to academic and industrial synthesis plans for vanillin as a case study

• John Andraos

Beilstein J. Org. Chem. 2020, 16, 2346–2362, doi:10.3762/bjoc.16.196

• alphabetical order along with temperature and pressure conditions for each reaction step. Table 2 summarizes the same alphabetized list showing the plan codes, starting materials used, and type of chemical process employed. Four plans involved biofermentation from ᴅ-glucose, ferulic acid, or isoeugenol [26][27

• ][28][29][30]; five plans involved chemical synthesis from wood-derived starting materials (lignosulfonic acid liquor or sawdust) [31][32][33][34][35][36][37]; seven plans involved chemical synthesis from either fossil-fuel or natural product-derived starting materials (guaiacol, eugenol, isoeugenol

• ] and other cellulosic biomass feedstocks, respectively. Isoeugenol and eugenol were chosen to originate from the natural product clover oil since 80% by weight of this essential oil is eugenol [48], and isoeugenol is directly obtained from eugenol by base-catalyzed isomerization. (5) Oxygen from air

Mechanochemical synthesis of graphene oxide-supported transition metal catalysts for the oxidation of isoeugenol to vanillin

• Ana Franco,
• Sudipta De,
• Alina M. Balu,
• Araceli Garcia and
• Rafael Luque

Beilstein J. Org. Chem. 2017, 13, 1439–1445, doi:10.3762/bjoc.13.141

• starting materials. To overcome this problem, lignin-derived monomers (such as eugenol, isoeugenol, ferulic acid etc.) have been effectively used in the past few years. However, selective and efficient production of vanillin from these feedstocks still remains an issue to replace the existing process. In

• this work, new transition metal-based catalysts were proposed to investigate their efficiency in vanillin production. Reduced graphene oxide supported Fe and Co catalysts showed high conversion of isoeugenol under mild reaction conditions using H2O2 as oxidizing agent. Fe catalysts were more selective

• as compared to Co catalysts, providing a 63% vanillin selectivity at 61% conversion in 2 h. The mechanochemical process was demonstrated as an effective approach to prepare supported metal catalysts that exhibited high activity for the production of vanillin from isoeugenol. Keywords: H2O2

Effect of cyclodextrin complexation on phenylpropanoids’ solubility and antioxidant activity

• Miriana Kfoury,
• David Landy,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2014, 10, 2322–2331, doi:10.3762/bjoc.10.241

• complex structure. Finally, the effect of complexation on the radical scavenging activity of PPs was investigated. Results and Discussion Formation constants (Kf) The complexation behavior of PPs including four phenylpropenes (trans-anethole (1), estragole (2), isoeugenol (3) and eugenol (4)) and three

• . Isoeugenol (3), eugenol (4), caffeic acid (6) and ferulic acid (7) reacted rapidly with DPPH• while trans-anethole (1), estragole (2) and p-coumaric acid (5) had a slow kinetic behavior. These observations were consistent with the literature data [42]. Results obtained in the absence and presence of CDs, are

• presented in Figure 5. Isoeugenol (3), eugenol (4), p-coumaric acid (5), caffeic acid (6) and ferulic acid (7) presented higher antioxidant activity than trans-anethole (1) and estragole (2). It is well known that the antioxidant activity of phenolic compounds such as PPs depends mainly on the degree of

Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome

• Amitabh Jha,
• Ting-Yi Chou,
• Zainab ALJaroudi,
• Bobby D. Ellis and
• T. Stanley Cameron

Beilstein J. Org. Chem. 2014, 10, 848–857, doi:10.3762/bjoc.10.81

• isoindolo[2,1-a]quinolone derivatives involves N-acyliminium ions or appropriate electron-deficient Schiff bases and subsequent [4 + 2] inverse-demand hetero-Diels–Alder cycloadditions with alkenes [11][12][13][14][15][16][17]. Vinylic systems from isoeugenol [11], cyclopentadiene [12], enones [13], vinyl