Smelling sulfur

Armstrong, Gavin

doi:10.1038/nchem.1322

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-[23-bis(tert-butoxycarbonyl)guanidino]propyne1

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2015

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“…Important Notes All guanidinylation reactions using N,Nʹ-bis(Boc)-Smethylisothiourea (2) produce methanethiol. [41] For this reason all evaporations were performed within the confines of a fume cupboard. Additionally, all glassware that was used during these procedures was soaked in H2O/bleach for a period of no less than 2 hours prior to regular cleaning.…”

Section: -[23-bis(tert-butoxycarbonyl)guanidino]propynementioning

confidence: 99%

Facile Synthesis of Guanidine Functionalised Building Blocks

2015

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Three useful developments in the preparation of guanidines are presented herein; i) a collection of bis(Boc)aminoalkylguanidines (n = 2, 3, 4 and 6), known to be prone to cyclisation, have been synthesised and isolated (without chromatography) as shelf stable sulfonate salts in good yield (up to 94%); ii) a selection of guanidines tethered to a range of other functional groups (including alkyne, alkene, alcohol and azide) have been prepared in good yields with no requirement for a purification step; and iii) an inexpensive, high-yielding (93%) and facile synthesis of N,Nʹ-bis(Boc)guanidine (a key precursor for N,Nʹ-bis(Boc)-Nʺ-triflylguanidine) is described in which the need for chromatographic purification is again obviated.

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Section: -[23-bis(tert-butoxycarbonyl)guanidino]propynementioning

confidence: 99%