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 man made 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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Additional info for The Sulphonium Group: Volume 2 (1981)
Removal of 1,3-dithiolane protective groups via ditholanium salts also has been accomplished with mesitylsulphonylhydroxylamine-water (equation 147)302 or benzeneseleninic anhydride (equation 148)303. Ring expansion of the 1,3-ditholium ring via the S-amino salt has been observed (equation 149)304. I H ClOz OH R' R 2 C 0 + (PhSe)2 + -fSCH2CH2SO2* (1481 434 Donald C. Dittmer and Bhalchandra H. Patwardhan EsH3 CINHCOzCzH5 * 1,3-Dithiolanium salts in which the positive charge is delocalized between the two sulphur atoms can be prepared in the following ways: (1) Addition of electrophiles to a 1,3-dithiolane with an exocyclic doubly bonded function ..
Some variation in regioselectivity of attack dependent on the nature of the nucleophile has been observedz2. Nucleophilic attack apparently can occur readily even at a neopentyl carbon if it is a member of a thiiranium ring13. T h e stereospecificity of the ring opening and lack of rearrangement seems to weigh against an open carbonium ion intermediate (equation 43). ’-st-”” R4 Nu Chloride and bromide ions demethylate S-methylthiiranium salts, derived from adarnantylideneadamantane, to give the thiiranZZb;this reaction is the first of its type.
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.
The Sulphonium Group: Volume 2 (1981)