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. 2006 Dec 1;2006(24):5076-5080.
doi: 10.1002/ejic.200600799.

A Facile Synthesis of Carbamoylsilanes, -boranes and -phosphane Oxides - Isolation of the First Uncomplexed Carbamoylborane

Yves Canac  1 , Greg E Aniol, Salvador Conejero, Bruno Donnadieu, Guy Bertrand
Affiliations

A Facile Synthesis of Carbamoylsilanes, -boranes and -phosphane Oxides - Isolation of the First Uncomplexed Carbamoylborane

Yves Canac et al. Eur J Inorg Chem. .

Abstract

C-(Trimethylsilyloxy)-, C-(triisopropylsilyloxy)-, C-(diphenylboryloxy), C-[bis(diisopropylamino)boryloxy]- and C-(di-tert-butylphosphoryloxy)-N,N-diisopropylaldiminium salts are readily prepared in good to excellent yields from either diisopropylformamide or (chloromethylene)diisopropylammonium chloride. Deprotonation of these aldiminium salts leads to transient (amino)(oxy)carbenes, which cleanly rearrange to carbamoyl derivatives. This synthetic methodology gives access to sterically hindered carbamoylsilanes, -boranes and phosphane oxides that are hardly accessible by other routes.

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Figures

Figure 1
Figure 1
Molecular view of the crystal structure of 2d (H atoms omitted). Selected bond lengths [Å] and angles [°]: B1–N2 1.4394(17), B1–N3 1.4223(17), B1–C1 1.6185(18), C1–O1 1.2449(14), C1–N1 1.3644(15); N3–B1–N2 124.35(11), N3–B1–C1 116.22(11), N2–B1–C1 119.31(11), O1–C1–N1 121.04(11), O1–C1–B1 118.54(10), N1–C1–B1 120.43(10), C1–N1–C5 120.89(10), C1–N1–C2 121.91(10), C5–N1–C2 117.07(10), B1–N2–C11 122.20(10), B1–N2–C8 122.68(10), C11–N2–C8 114.98(10), B1–N3–C17 120.08(10), B1–N3–C14 118.84(10), C17–N3–C14 120.33(10).
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
See this image and copyright information in PMC

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