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van Leeuwen, P. W. N. M.: 2014 Science of Synthesis, 2013/8: C-1 Building Blocks in Organic Synthesis 2 DOI: 10.1055/sos-SD-213-00080
C-1 Building Blocks in Organic Synthesis 2

2.3.1 Carbene Insertion into C—H Bonds with C-1

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Editor: van Leeuwen, P. W. N. M.

Authors: Ballini, R.; Belderrain, T. R.; Bruneau, C.; Cokoja, M.; Dong, D.; Fischmeister, C.; Grushin, V. V.; Hu, J.; Ibrahim, H.; Iwasawa, N.; Kaposi, M.; Kühn, F. E.; Lishchynskyi, A.; Merino, P.; Molander, G. A.; Müller, C.; MuÇoz-Molina, J. M.; Neumann, H.; Ni, C.; Nicasio, M. C.; Novák, P.; Nozaki, K.; Ouali, A.; Petrini, M.; Rutjes, F. P. J. T.; Ryu, D.; Schoonen, L.; Schranck, J.; Taillefer, M.; Takahashi, K.; Takaya, J.; te Grotenhuis, C.; Witt, J.; Zhang, N.

Title: C-1 Building Blocks in Organic Synthesis 2

Subtitle: Alkenations, Cross Couplings, Insertions, Substitutions, and Halomethylations

Print ISBN: 9783131751218; Online ISBN: 9783132064515; Book DOI: 10.1055/b-003-125817

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: C-1 Building Blocks in Organic Synthesis

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

Treatment of a diazo compound, i.e. a (diazomethyl)phosphonate or diazo(trimethylsilyl)methane, with a base, and subsequent alkenation of a carbonyl compound (Wittig–Horner reaction or Peterson elimination), followed by decomposition of the resulting diazoalkene affords an alkylidene carbene. This species may undergo intramolecular C—H insertion to generate five-membered carbocyclic or heterocyclic systems. In this chapter, some applications of this methodology in organic synthesis are reviewed.

Key words

diazo compounds - diazo(trimethylsilyl)methane - diethyl (diazomethyl)phosphonate - alkylidene carbenes - C—H insertion reactions - cyclopentenes - 2,5-dihydrofurans - 2,5-dihydropyrroles
 
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