2-Alkoxy-2-amino-Δ<sup>3</sup>-1,3,4-oxadiazolines as Novel Sources of Alkoxyaminocarbenes

Couture, Philippe; Terlouw, Johan K.; Warkentin, John

doi:10.1021/ja953813+

Cited by 58 publications

(22 citation statements)

References 21 publications

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“…[124] 2.3.6. Cyclic Alkyl(amino)carbenes (CAACs) Some years before the preparation of the first N-heterocyclic carbene by Arduengo et al [30] Bertrand et al described the stable (trimethylsilyl)[bis(diisopropylamino)phosphanyl]carbene 35 [8] and shortly thereafter the molecular structure of a crystalline phosphanyl(silyl)carbene [125] The stable noncyclic heteroatom-stabilized carbenes 36, [9] 37, [126] 38, [127] 39, [128] and 40 [129] have also been prepared (Scheme 43). [130] The synthesis of the phosphanyl(aryl)carbene 41 [131] marked the entrance into the chemistry of stable singlet carbenes which are stabilized by only one heteroatom.…”

Section: Heterocyclic Carbenesmentioning

confidence: 99%

Heterocyclic Carbenes: Synthesis and Coordination Chemistry

2008

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The chemistry of heterocyclic carbenes has experienced a rapid development over the last years. In addition to the imidazolin-2-ylidenes, a large number of cyclic diaminocarbenes with different ring sizes have been described. Aside from diaminocarbenes, P-heterocyclic carbenes, and derivatives with only one, or even no heteroatom within the carbene ring are known. New methods for the synthesis of complexes with N-heterocyclic carbene ligands such as the oxidative addition or the metal atom template controlled cyclization of beta-functionalized isocyanides have been developed recently. This review summarizes the new developments regarding the synthesis of N-heterocyclic carbenes and their metal complexes.

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Section: Heterocyclic Carbenesmentioning

confidence: 99%

Heterocyclic Carbenes: Synthesis and Coordination Chemistry

2008

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“…Selected bond distances (Å) and angles (deg). 5a: P1-C1 1.9010(13), C1-N1 1.4164 (16), P1-C1-C2 102.83(8), P1-C1-N1 123.34(10), C2-C1-N1 119.21 (11), C1-N1-C14 118.85(11), C1-N1-C11 123.02(11), C11-N1-C14 116.38 (12). 6a: P1-C1 1.695(2), C1-N1 1.422(3), P1-C1-C2 109.98 (16), P1-C1-N1 128.69 (18), C2-C1-N1 121.03 (19), C1-N1-C9 122.7(2), C1-N1-C12 118.67 (19), C9-N1-C12 115.8(2).…”

Section: Crystal Structure Determination Of Compounds 5a and 6amentioning

confidence: 99%

Synthesis of Transient and Stable C-Amino Phosphorus Ylides and Their Fragmentation into Transient and Stable Carbenes

et al. 2005

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Only basic phosphines, such as tris(dimethylamino)phosphine, allow for the synthesis of a stable acyclic beta-amino phosphonium salt 1c, which upon deprotonation with butyllithium affords the corresponding stable C-amino phosphorus ylide 2c. In contrast, cyclic beta-amino phosphonium salts 5a and 5b are stable despite the presence of weakly basic triarylphosphine fragments. They are prepared by intramolecular insertion of the carbene center of (amino)(phosphonio)carbenes into the CH bond of a phosphorus substituent. Deprotonation of 5a leads to the corresponding cyclic C-amino phosphorus ylide 6a, which has been fully characterized including an X-ray diffraction study. Deprotonation of 5b affords enamine 8, probably via fragmentation of ylide 6b into transient carbene 7b and a subsequent 1,2-hydrogen shift. Transient cyclic C-amino phosphorus ylides 6c and 6d have been prepared by intramolecular addition of a carbanion generated by deprotonation of a phosphorus substituent. Three-membered heterocycle 6c rearranges into alkene 9, whereas the four-membered ring system undergoes a ring opening affording the stable carbene 7d. The latter results pave the route for the synthesis of various mixed carbene-phosphine bidentate ligands.

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“…However, spirocyclic analogues are available from modified ketone semicarbazones (Scheme 3). 12- 15 The difference in stability of the cyclic and acyclic amino(oxy)oxadiazolines is probably entropic, at least in part. Ring opening of the spirocyclic species is more likely to be reversible, the reclosure being an intramolecular reaction.…”

Section: Oxidative Cyclization Of Ketone Hydrazonesmentioning

confidence: 99%

Δ3-1,3,4-Oxadiazolines.† Versatile sources of reactive intermediates

Warkentin

2000

J. Chem. Soc., Perkin Trans. 1

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2-Alkoxy-2-amino-Δ³-1,3,4-oxadiazolines as Novel Sources of Alkoxyaminocarbenes

Cited by 58 publications

References 21 publications

Heterocyclic Carbenes: Synthesis and Coordination Chemistry

Heterocyclic Carbenes: Synthesis and Coordination Chemistry

Synthesis of Transient and Stable C-Amino Phosphorus Ylides and Their Fragmentation into Transient and Stable Carbenes

Δ3-1,3,4-Oxadiazolines.† Versatile sources of reactive intermediates

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2-Alkoxy-2-amino-Δ3-1,3,4-oxadiazolines as Novel Sources of Alkoxyaminocarbenes

Cited by 58 publications

References 21 publications

Heterocyclic Carbenes: Synthesis and Coordination Chemistry

Heterocyclic Carbenes: Synthesis and Coordination Chemistry

Synthesis of Transient and Stable C-Amino Phosphorus Ylides and Their Fragmentation into Transient and Stable Carbenes

Δ3-1,3,4-Oxadiazolines.† Versatile sources of reactive intermediates

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2-Alkoxy-2-amino-Δ³-1,3,4-oxadiazolines as Novel Sources of Alkoxyaminocarbenes