Stoichiometric and catalytic conversion of 1-adamantyl azide to 1-adamantyl isocyanate by [Cr(CO) 3Cp] 2 and reaction with Mo(CO) 3(P iPr 3) 2 to form Mo(κ 2- iPr 3P=NN=NAd)(CO) 3(P iPr 3)

George C. Fortman, Burjor Captain, Carl Hoff

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The reaction of 1-adamantyl azide (N 3Ad) with [Cr(CO) 3Cp] 2 under Ar results in conversion of N 3Ad to 1-adamantyl isocyanate (OCNAd) and [Cr(CO) 2Cp] 2. Two reaction intermediates were detected: 3Cr 2(CO) 5Cp 2 and an electron spin resonance active complex proposed to be Cr(CO) 2(O-C-NAd)Cp. Under a CO atmosphere, 3Cr 2(CO) 5Cp 2 regenerates [Cr(CO) 3Cp] 2 and approximately five turnovers can be achieved. Hydrogenation of N 3Ad by HMo(CO) 3Cp yields H 2NAd, N 2, and [Mo(CO) 3Cp] 2. N 3Adreacts with Mo(CO) 3(P iPr 3) to form Mo(N 3Ad)(CO) 3(P iPr 3) 2, which slowly isomerizes to Mo(κ 2-Pr 3PN 3Ad)(CO) 3(P iPr 3), the structure of which is reported.

Original languageEnglish
Pages (from-to)3587-3590
Number of pages4
JournalOrganometallics
Volume28
Issue number13
DOIs
StatePublished - Jul 13 2009

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Isocyanates
isocyanates
reaction intermediates
Azides
Carbon Monoxide
hydrogenation
electron paramagnetic resonance
atmospheres
Reaction intermediates
Hydrogenation
Paramagnetic resonance

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

Cite this

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title = "Stoichiometric and catalytic conversion of 1-adamantyl azide to 1-adamantyl isocyanate by [Cr(CO) 3Cp] 2 and reaction with Mo(CO) 3(P iPr 3) 2 to form Mo(κ 2- iPr 3P=NN=NAd)(CO) 3(P iPr 3)",
abstract = "The reaction of 1-adamantyl azide (N 3Ad) with [Cr(CO) 3Cp] 2 under Ar results in conversion of N 3Ad to 1-adamantyl isocyanate (OCNAd) and [Cr(CO) 2Cp] 2. Two reaction intermediates were detected: 3Cr 2(CO) 5Cp 2 and an electron spin resonance active complex proposed to be Cr(CO) 2(O-C-NAd)Cp. Under a CO atmosphere, 3Cr 2(CO) 5Cp 2 regenerates [Cr(CO) 3Cp] 2 and approximately five turnovers can be achieved. Hydrogenation of N 3Ad by HMo(CO) 3Cp yields H 2NAd, N 2, and [Mo(CO) 3Cp] 2. N 3Adreacts with Mo(CO) 3(P iPr 3) to form Mo(N 3Ad)(CO) 3(P iPr 3) 2, which slowly isomerizes to Mo(κ 2-Pr 3PN 3Ad)(CO) 3(P iPr 3), the structure of which is reported.",
author = "Fortman, {George C.} and Burjor Captain and Carl Hoff",
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T1 - Stoichiometric and catalytic conversion of 1-adamantyl azide to 1-adamantyl isocyanate by [Cr(CO) 3Cp] 2 and reaction with Mo(CO) 3(P iPr 3) 2 to form Mo(κ 2- iPr 3P=NN=NAd)(CO) 3(P iPr 3)

AU - Fortman, George C.

AU - Captain, Burjor

AU - Hoff, Carl

PY - 2009/7/13

Y1 - 2009/7/13

N2 - The reaction of 1-adamantyl azide (N 3Ad) with [Cr(CO) 3Cp] 2 under Ar results in conversion of N 3Ad to 1-adamantyl isocyanate (OCNAd) and [Cr(CO) 2Cp] 2. Two reaction intermediates were detected: 3Cr 2(CO) 5Cp 2 and an electron spin resonance active complex proposed to be Cr(CO) 2(O-C-NAd)Cp. Under a CO atmosphere, 3Cr 2(CO) 5Cp 2 regenerates [Cr(CO) 3Cp] 2 and approximately five turnovers can be achieved. Hydrogenation of N 3Ad by HMo(CO) 3Cp yields H 2NAd, N 2, and [Mo(CO) 3Cp] 2. N 3Adreacts with Mo(CO) 3(P iPr 3) to form Mo(N 3Ad)(CO) 3(P iPr 3) 2, which slowly isomerizes to Mo(κ 2-Pr 3PN 3Ad)(CO) 3(P iPr 3), the structure of which is reported.

AB - The reaction of 1-adamantyl azide (N 3Ad) with [Cr(CO) 3Cp] 2 under Ar results in conversion of N 3Ad to 1-adamantyl isocyanate (OCNAd) and [Cr(CO) 2Cp] 2. Two reaction intermediates were detected: 3Cr 2(CO) 5Cp 2 and an electron spin resonance active complex proposed to be Cr(CO) 2(O-C-NAd)Cp. Under a CO atmosphere, 3Cr 2(CO) 5Cp 2 regenerates [Cr(CO) 3Cp] 2 and approximately five turnovers can be achieved. Hydrogenation of N 3Ad by HMo(CO) 3Cp yields H 2NAd, N 2, and [Mo(CO) 3Cp] 2. N 3Adreacts with Mo(CO) 3(P iPr 3) to form Mo(N 3Ad)(CO) 3(P iPr 3) 2, which slowly isomerizes to Mo(κ 2-Pr 3PN 3Ad)(CO) 3(P iPr 3), the structure of which is reported.

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