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22nd August 2013 @ 15:27

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Reaction information

*#Reaction file  
*Reaction file type CDX

General procedure C (see below) with N-(Hex-1-yn-1-yl)-4-methyl-N-(non-8-en-3-yn-1-yl)benzenesulfonamide (372 mg, 1.0 mmol).  Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave the product as a pale yellow oil (119 mg, 32%).

The major product (title compound) was (E)‑N‑(hex‑1‑yn‑1‑yl)‑4‑methyl‑N‑(3‑(2‑methylcyclopentylidene)propyl)benzenesulfonamide (136a) obtained as a pale yellow oil (150 mg, 40%)



General procedure C: zirconocene mediated cocyclisation of ynamides

n-BuLi (0.88 mL of a 2.5 M solution in hexanes, 2.2 mmol) was added dropwise to a solution of Cp2ZrCl2 (322 mg, 1.1 mmol) in dry THF (5.0 mL) at −78 °C.  A solution of the appropriate ynamide (1.0 mmol) in dry THF (3.0 mL) was added dropwise at −78 °C.  The reaction mixture was warmed to room temperature and stirred for 5 h.  The reaction mixture was cooled to −78 °C and MeOH (10.0 mL) added.  After stirring at −78 °C for 1 h the reaction mixture was stirred at room temperature for 16 h.  The reaction mixture was poured into water (100 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed sequentially with water (2 × 100 mL) and brine (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product, which was purified as described.

*Yield (%)  40
*Type of Yield Isolated product yield
AH Thesis_2011_pp106.pdf
AH Thesis_2011_pp176-223.pdf
Further information  Compound 136b: (E)‑N‑(hex‑1‑yn‑1‑yl)‑4‑methyl‑N‑(3‑(2‑methylcyclohexylidene)propyl)benzenesulfonamide

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Overall reaction? True
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Attached Files
AH Thesis_2011_pp106.pdf
AH Thesis_2011_pp176-223.pdf