Pentane → 134938-21-9

HRID 1653937Notes

Reaction equation

HRID 1653937 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][CH2:9][CH2:10][CH2:11][CH3:12]>>[C:2]1([C:9]23[CH2:12][CH:11]([CH2:8]2)[CH2:10]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8003PentaneHCID 11575Iodobenzene

Product 1

HCID 10606871134938-21-9

Procedure

1.28 ml (0.5 e.g.) of iodobenzene were added to a solution of propellane (10 mmol) generated via Procedure B. The solution was transferred into a borosilicate tube and irradiated 1 hr, after which GC analysis of the solution showed three new major peaks. The reaction mixture was reduced in volume, high vacuum applied (40° C./0.2 mm Hg) to remove starting material and 1-iodobicyclo[1.1.1]pentane. After these products were removed, 1-iodo-3-phenylbicyclo[1.1.1]pentane sublimed out of the mixture (40°-50° C./0.2 mm Hg): 1H NMR 2.06 (s, 6H); EIMS, m/z (relative intensity) 77(24), 127(25), 128(100), 143(91). Resublimation produced an analytical sample having mp. 64°-65° C. Recrystallization from penfane at 0° C. gave a gummy solid. The liquid was diluted with pentane and recrystallization at -78° C., giving 1-phenylbicyclo[1.1.1]pentane: The solid, a mixture of 1-phenyl]2]staffane and 3-iodo-3'-phenyl[2]staffane by GCMS, was recrystallized from benzene.

Workup

  1. customThe solution was transferred into a borosilicate tube
  2. customirradiated 1 hr
  3. custom(40° C./0.2 mm Hg)
  4. customto remove
  5. customAfter these products were removed
  6. customsublimed out of the mixture (40°-50° C./0.2 mm Hg)
  7. customResublimation produced an analytical sample
  8. customRecrystallization from penfane at 0° C.
  9. customgave a gummy solid

Sources & evidence

ORD record
ord-1d8532b605334835aebd2682b3bdd696
Source dataset
uspto-grants-1995_04
Patent number
US05405550

Reaction notes

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