Oxygen → HCID 20481874, compound

HRID 851338Notes

Reaction equation

HRID 851338 reaction equation
[F:1][C:2]([F:17])([C:5]([F:16])([F:15])[O:6][C:7]([F:14])([F:13])[C:8]([F:12])=[C:9]([F:11])[F:10])[C:3]#[N:4].[O:18]=O>>[F:1][C:2]([F:17])([C:5]([F:15])([F:16])[O:6][C:7]([F:14])([F:13])[C:8]1([F:12])[O:18][C:9]1([F:11])[F:10])[C:3]#[N:4]

Participants

3

Reactant 2

HCID 977OxygenHCID 88462806HCID 88462806, compound

Product 1

HCID 20481874HCID 20481874, compound

Procedure

A 100-ml stainless steel-lined tube charged with 38.5 g (0.14 mol) of perfluoro-4-oxa-6-heptenenitrile was heated at 140° while oxygen was added incrementally (over 5.5 h) until reaction was complete. Fractionation of the liquid products gave perfluoro-6,7-epoxy-4-oxaheptanenitrile, bp 65°-67°, 15.7 g (39%). IR (CCl4); 4.40 (CN), 6.47 (epoxide) and 8-9μ (CF, C-O). NMR (CCl4): -87.5 (m, 2F, OCF2), -109.2 (t, JFF 4.7 Hz, 2F, CF2CN), and -156.7 ppm (d of d of m, JFF 18.7, 16.7 Hz, 1F, CF) with AB groupings for ring CF2 at -10347 and -10389 Hz (d of t, JFF 18.7, 9.5 Hz, 1F) and -10570 and -10610 Hz (d, JFF 16.7 Hz, 1F) and for CF2 adjacent to epoxide ring at -7376, -7529, -7556, and -7707 Hz (m, 2F).

Workup

  1. additionwas added incrementally (over 5.5 h)
  2. customuntil reaction

Sources & evidence

ORD record
ord-433b19dea738420e8423399319bcc62c
Source dataset
uspto-grants-1983_05
Patent number
US04384128

Reaction notes

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