4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH): a new chromophoric reagent for quantitative monitoring of solid-phase aldehydes(1-3)

The Journal of Organic Chemistry
Simon K Shannon, G Barany

Abstract

A direct method for quantifying solid-phase aldehydes has been developed, using a new reagent, 4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH). The FmPH reagent was synthesized in three steps (24% overall yield) from commercially available p-hydrazinobenzoic acid. Resin-bound aldehydes reacted quantitatively with FmPH, in the presence of trimethylorthoformate (TMOF) as a dehydrating agent, to form a highly conjugated, immobilized FmPH-hydrazone. Next, mild treatment of the hydrazone with an excess of piperidine-N,N-dimethylformamide (1:1) released the piperidine-dibenzofulvene adduct chromophore (epsilon(301nm) = 7800 M(-1) cm(-1)) from the support. FmPH quantitation of aldehydes proved to be a straightforward, sensitive, and reproducible technique for monitoring resin-bound aldehydes [albeit insufficiently reactive to allow reliable quantification of ketones]. The FmPH aldehyde assay is applicable to a range of solid supports, as demonstrated specifically for poly(ethylene glycol)-polystyrene (PEG-PS), aminomethylpolystyrene (AMP), and cross-linked ethoxylate acrylate resin (CLEAR).

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Citations

Nov 18, 2005·Chemical Communications : Chem Comm·Stefan Sommer, Herbert Waldmann
Feb 3, 2007·Chemical Communications : Chem Comm·Ana B GarciaHerbert Waldmann
Nov 5, 2010·Organic & Biomolecular Chemistry·Marie W JohannsenJesper Wengel
Mar 18, 2009·Chemical Reviews·Ulrik BoasKnud J Jensen
Oct 6, 2007·Langmuir : the ACS Journal of Surfaces and Colloids·Mahsa GhasemiFarzaneh Arefi-Khonsari
Nov 15, 2005·Journal of Combinatorial Chemistry·Roland E Dolle

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