adj-Dicarbaporphyrinoid Systems: Synthesis, Spectroscopic Characterization, and Reactivity of 23-Carbabenziporphyrins was written by Jain, Pankaj;AbuSalim, Deyaa I.;Lash, Timothy D.. And the article was included in Journal of Organic Chemistry in 2019.Safety of 3-Iodo-4-methoxybenzaldehyde This article mentions the following:
A new family of adj-dicarbaporphyrinoids has been prepared using the “2 + 2” MacDonald methodol. Dibutylboron triflate catalyzed condensation of 3-iodo-4-methoxybenzaldehyde with an indene enamine afforded an iodofulvene aldehyde; and a related dimethoxyfulvene was similarly prepared in two steps from 2,4-dimethoxybenzaldehyde. Following protection as the corresponding di-Me acetals, the iodofulvenes were metalated with Bu3MgLi at -100 °C and reacted with DMF to give the required fulvene dialdehyde intermediates. Acid-catalyzed condensation with three different dipyrrylmethanes afforded a series of benzo-23-carbabenziporphyrins I (R = Et, Me, CH2CH2CO2Me, X = H; R = Et, Me, CH2CH2CO2Me, X = OMe) in 52-70% yields. The proton NMR spectra for these adj-dicarbaporphyrinoids indicate that these macrocycles are slightly diatropic. Monoprotonation afforded cationic species with slightly larger aromatic ring currents, and under strongly acidic conditions, C-protonated dications were generated with substantial diatropic properties. The aromatic character of these structures was supported by nucleus-independent chem. shifts and anisotropy of induced c.d. calculations The computational results indicate that the dications favor 23-atom 22π electron delocalization pathways. The benzo-23-carbabenziporphyrins were selectively oxidized with silver(I) acetate in dichloromethane-methanol to give stable nonaromatic structures with two addnl. methoxy substituents connected to sp3 hybridized bridging carbons. The intriguing reactivity and unique spectroscopic properties of benzo-23-carbabenziporphyrins make these novel structures promising candidates for further investigations. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Safety of 3-Iodo-4-methoxybenzaldehyde).
3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Iodo alkanes participate in a variety of organic synthesis reactions, which include the SimmonsSmith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Safety of 3-Iodo-4-methoxybenzaldehyde
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com