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. 2010 Aug 18;6:880–921. doi: 10.3762/bjoc.6.88

Table 1.

Interaction of thiophenols with perfluoroalkyl iodides in liquid ammonia under UV irradiation.

graphic file with name Beilstein_J_Org_Chem-06-880-i002.jpg

R RF Yields of ArSRF, % Ref.

H CF3 76 [143]
C2F5, n-C3F7, iso-C3F7 84, 81, 76 [144]
4-NH2 CF3 87 [146]
2-NH2 CF3 71 [143]
4-OH CF3 69.5 [143]
2-OCH3 CF3 86 [98]
4-Cl CF3 72 [146]
C2F5, n-C3F7, iso-C3F7 84, 83, 65 [144]
2-SO2CHF2 CF3 69 [143,146]
4-SO2CF3 CF3 78 [143,146]
4-NO2 CF3 2.7a [143,146]
63b [143,146]
2,4-Cl2 CF3 87 [149]
C3F7 89 [149]
2-COOH CF3 90 [150]
3- and 4-COOCH3 CF3, n-C3F7, iso-C3F7 70–80 [151]
3- and 4-F CF3, n-C3F7 80–90 [152]
iso-C3F7 72–75 [152]
4-NHCOCH3 CF3 96 [153]
4-NHCOOCH3 CF3, n-C3F7 88 (92c), 82 (93c) [9]
C2F5, C4F9 62, 55 [154]

aIn a quartz flask.

bIn a quartz ampoule at 30–45 °C.

cWith preliminary reduction of 4,4′-bis(MeOCONH)diaryl disulfide and without the isolation of corresponding thiophenol.