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is used to introduce the FMOC protecting group. Chloroformates are popular in the field of chromatography as derivatization agents. They convert polar compounds into less polar more volatile derivatives. In this way, chloroformates enable relatively simple transformation of large array of metabolites
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Hušsek, Petr; Šimek, Petr (2006). "Alkyl
Chloroformates in Sample Derivatization Strategies for GC Analysis. Review on a Decade Use of the Reagents as Esterifying Agents".
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Typically these reactions would be conducted in the presence of a base which serves to absorb the HCl.
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46:. Most are colorless, volatile liquids that degrade in moist air. A simple example is
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Alkyl chloroformate esters degrate to give the alkyl chloride, with retention of
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Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
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Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
227:(6th ed.), New York: Wiley-Interscience, p. 1428,
257:(6th ed.), New York: Wiley-Interscience, p. 468,
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27:General chemical structure of chloroformate esters
38:with the formula ROC(O)Cl. They are formally
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61:is used to introduce the Cbz (carboxybenzyl)
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82:are similar. Representative reactions are:
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169:The reaction is proposed to proceed via a
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78:The reactivity of chloroformates and
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57:in organic chemistry. For example,
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171:substitution nucleophilic internal
121:ROC(O)Cl + HOR' → ROC(O)-OR' + HCl
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192:Current Pharmaceutical Analysis
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294:. You can help Knowledge by
144:CR' → ROC(O)−OC(O)R' + HCl
53:Chloroformates are used as
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204:10.2174/157341206775474007
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161:ROC(O)Cl ' → RCl + CO
103:NR' → ROC(O)-N(H)R' + HCl
16:Not to be confused with
341:Organic chemistry stubs
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59:benzyl chloroformate
48:methyl chloroformate
247:Smith, Michael B.;
217:Smith, Michael B.;
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351:Functional groups
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264:978-0-471-72091-1
234:978-0-471-72091-1
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198:: 23-43.
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251:(2007),
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