Chapter thirteen Cyclic sulphonium salts (pages 387–521): Donald C. Dittmer and Bhalchandra H. Patwardhan
Chapter 14 Qrganosulphur cation radicals (pages 523–570): Henry J. Shine
Chapter three Heterosulphonium salts (pages 571–672): Shigeru Oae, Tatsuo Numata and Toshiaki Yoshimura
Chapter sixteen artificial purposes of sulphonium salts and sulphonium ylides (pages 673–702): Eric Block
Chapter 17 The biochemistry of sulphonium salts (pages 703–770): G. A. Maw
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Extra resources for The Sulphonium Group: Volume 2 (1981)
Equations 62I6l and 63162. A+ S-S N/ A N’ * H -P Ar-S -2s Anode * + R’ Ar-$XR2 - -s S Ar : NU Ar/ 111. FOUR-MEMBERED RINGS A. Saturated Rings 1 . Reviews Two reviews on thietanes have touched briefly on cyclic, four-membered sulphonium s a l t ~ ’ ~ ~ J ~ . 2. Stable thietaniurn salts Treatment of thietane with methyl iodide originally was believed to yield a bis-methylated thietanium salt’65, but subsequently it was shown that ring opening had occurred and that the compound obtained was dimethyL(3-iodopropy1)sulphonium iodide166.
Interestingly, the four a-methylene ring protons in I-ethylthietanium tetrafluoroborate exchange very rapidly but the a-methylene protons of the ethyl group are not readily exchanged. The proton exchange in four-membered sulphonium ions is approximately 100-times faster than exchange in sulphonium ions of larger ring size. The faster rate was attributed to more s-character in the bonding from sulphur to carbon in the four-membered compounds; this increase in s-character was expected to have an acidifying effect on the protons attached to the a-carbon atoms.
P h e P h I R H ao, = Ph)$-Ph NIH H+ R ' (89) Donald C. Dittmer and Bhalchandra H. Patwardhan 420 ph)-y-ph 0 Ph CH3 ClO, II Ph-S-CH-CH2-C-CH3 I H20 & - HH20 C104 cH3q-;: (90) H H ClO, Nucleophilic attack on thiacyclobuienonium ion intermediates by water causes ring opening (equations 91202 and 92203a). 3-Phenylthiete reacts readily with triethyloxonium tetrafluoroborate to yield the S-ethyl salt which undergoes both ring opening and dealkylation on treatment with n u c l e ~ p h i l e s ~ ~ ~ ~ .
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