Synthesis of porphyrins bearing 1-4 hydroxymethyl groups and other one-carbon oxygenic substituents in distinct patterns

Zhen Yao; Jayeeta Bhaumik; Savithri Dhanalekshmi; Marcin Ptaszek; Phillip A Rodriguez; Jonathan S Lindsey

doi:10.1016/j.tet.2007.07.108

Synthesis of porphyrins bearing 1-4 hydroxymethyl groups and other one-carbon oxygenic substituents in distinct patterns

Tetrahedron. 2007 Oct 22;63(43):10657-10670. doi: 10.1016/j.tet.2007.07.108.

Authors

Zhen Yao¹, Jayeeta Bhaumik, Savithri Dhanalekshmi, Marcin Ptaszek, Phillip A Rodriguez, Jonathan S Lindsey

Affiliation

¹ Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.

Abstract

Porphyrins that bear one-carbon oxygenic substituents (hydroxymethyl, formyl, ester) directly attached to the macrocycle afford a compact architecture that is attractive for diverse applications. Routes to 9 porphyrins bearing such groups in distinct architectures (A(4)-, trans-A(2)-, trans-A(2)B(2)-, trans-AB- and trans-AB(2)C-porphyrins) have been explored (A = hydroxymethyl), including porphyrins bearing two one-carbon units in different oxidation states (hydroxymethyl/ester, formyl/ester). The hydroxymethyl group was introduced via TBDMS-protected dipyrromethane precursors.

Abstract

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