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2,2,2-Trichloroethoxycarbonyl chloride

Trichloroethyl chloroformate

Trichloroethyl chloroformate is used in organic synthesis for the introduction of the trichloroethoxycarbonyl (Troc) protecting group for amines, thiols and alcohols. It readily cleaves in the presence of other carbamates.

The Troc group is traditionally removed via Zn insertion in the presence of acetic acid, resulting in elimination and decarboxylation.

Amine protection – 2,2,2-Trichloroethoxycarbonyl (Troc)

:[[File:Troc_protecting_group.png|thumb|left|Troc protecting group on an amine]] The 2,2,2-Trichloroethoxycarbonyl (Troc) group is largely used as a protecting group for amines in organic synthesis.

Most common amine protection methods

  • 2,2,2-Trichloroethyl chloroformate, pyridine or aqueous sodium hydroxide at ambient temperature :[[File:Troc_group_protection.png|left|400px]]

  • Electrolysis :[[File:Troelectrolysis.png|left|400px]]

  • Deprotection using zinc metal :[[File:Troc dep mod copy q.jpg|left|400px]]

References

References

  1. [http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/23258 2,2,2-Trichloroethyl chloroformate] {{Webarchive. link. (2012-09-09 at [[Sigma-Aldrich]])
  2. Marullo, N. P.. (1969-01-01). "Structural organic chemistry by nmr. III. Isomerization of compounds containing the carbon-nitrogen double bond". Tetrahedron Letters.
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chloroformates protecting-groups reagents-for-organic-chemistry
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