Specialist Periodical Reports provide systematic and detailed review coverage of progress in the major areas of chemical research. Written by experts in their specialist fields the series creates a unique service for the active research chemist, supplying regular critical in-depth accounts of progress in particular areas of chemistry. For over 80 years the Royal Society of Chemistry and its predecessor, the Chemical Society, have been publishing reports charting developments in chemistry, which originally took the form of Annual Reports. However, by 1967 the whole spectrum of chemistry could no longer be contained within one volume and the series Specialist Periodical Reports was born. The Annual Reports themselves still existed but were divided into two, and subsequently three, volumes covering Inorganic, Organic and Physical Chemistry. For more general coverage of the highlights in chemistry they remain a 'must'. Since that time the SPR series has altered according to the fluctuating degree of activity in various fields of chemistry. Some titles have remained unchanged, while others have altered their emphasis along with their titles; some have been combined under a new name whereas others have had to be discontinued. The current list of Specialist Periodical Reports can be seen on the inside flap of this volume.

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Organic Compounds of Sulphur, Selenium, and Tellurium Volume 5

A Review of the Literature Published Between April 1976 and March 1978

By D R Hogg

The Royal Society of Chemistry

Chapter 1 Aliphatic Organosulphur Compounds, Compounds with Exocyclic Sulphur Functional Groups, and their Selenium and Tellurium Analogues By G. C. Barrett, 1, 
Chapter 2 Ylides of Sulphur, Selenium, and Tellurium, and Related Structures By E. Block and M. Haake, 70, 
Chapter 3 Thiocarbonyl and Selenocarbonyl Compounds By D. R. Hogg, P. Metzner, J. Voss, and W. Walter, 118, 
Chapter 4 Small Ring Compounds of Sulphur and Selenium By F. A Davis, 187, 
Chapter 5 Saturated Cyclic Compounds of Sulphur and Selenium By A. Fava and E. Sandri, 213, 
Chapter 6 Thiophens and their Selenium and Tellurium Analogues By S. Gronowitz, 247, 
Chapter 7 Dithioles and Related Compounds By D. Leaver, 306, 
Chapter 8 ThiopyraAs and Related Compounds By U. Eisner, 324, 
Chapter 9 Thiepins and Dithiins By U. Eisner, 337, 
Chapter 10 Isothiazoles and Related Compounds By M. Davis, 345, 
Chapter 11 Thiazoles and Related Compounds By B. Iddon and P. A. Lowe, 358, 
Chapter 12 Condensed Ring Systems Incorporating Thiazole By B. Iddon and P.A. Lowe, 393, 
Chapter 13 Thiadiazoles and Selenadiazoles By M. Davis, 431, 
Chapter 14 (β-Lactam Antibiotics, other Sulphur-containing Natural Products, and Related Compounds By J. G. Gleason and W. D. Kingsbury, 454, 
Author Index, 481,

CHAPTER 1

Aliphatic Organosulphur Compounds, Compounds with Exocyclic Sulphur Functional Groups, and their Selenium and Tellurium Analogues

BY G. C. BARRETT

There has been an increase in the number of entries in Chemical Abstracts from 7.5 � 105, for the corresponding period reviewed for the previous volume in this series, to 7.85 � 105 for the current period. However, a more substantial increase has occurred in the number of papers eligible for citation in this chapter. The layout used in previous volumes is retained for this chapter, for which further compression of a larger number of references into a smaller number of pages has led to more terse descriptions of topics which have been dealt with more fully in previous volumes. Readers may therefore find it helpful to refer to previous volumes in this series when encountering discussion which has been severely compressed in parts of the present chapter.

1 Textbooks and Reviews

Textbook coverage of sulphur functional groups continues to keep pace with the increasing interest in organosulphur chemistry. Reviews have appeared dealing with organosulphur chemistry in general, sulphur-containing natural products, thiols (mercapto-ketones, 4-mercapto-azetidinones, heterocyclic thiols, estimation of SH groups in proteins), ylide formation from sulphides and carbenes, sulphuranes and selenuranes, 'umpolung' via sulphur-containing reagents, stereochemistry of sulphoxides, sulphones, triflones, thiocyanates, sulphoximines, nucleophilic substitution at tricoordinate sulphur, reaction of disulphides with tervalent phosphorus compounds, (O-mesitylenesulphonyl)hydroxylamine as an aminating agent,2q and named reactions in organosulphur chemistry. A thorough survey of modern organoselenium chemistry has appeared and also a review of the use of organoselenium reagents for the introduction of C=C bonds under mild conditions.

2 Characteristics of Sulphur Functional Groups

Methylthio- and phenylthio-groups have larger acidifying effects than would be calculated on the basis of polarizability, for the C-acids R1SCH2R2 in DMS0. Conjugative stabilization of the α-sulphenyl carbanion appears to be significant. This is a theme of continuing interest in theoretical terms, and is now seen to be a result of a greater two-electron stabilization of the whole carbanionic system of an α-alkylsulphenyl carbanion because of its enhanced electron-accepting ability compared with its oxygen analogue. (p-d)π Conjugation need not be postulated to explain this fact. The lone pair in an α-alkylselenenyl carbanion preferentially adopts an equatorial position due to anomeric-type stabilization involving the σ*-orbital of the Se — C bond. Stabilization by Se is ca. 3 kcal mol-1 greater than that by S in these systems, and specific d-orbital effects are not involved.

Based on X-ray crystallographic data, bivalent sulphur appears to prefer nucleophiles to approach along the direction of the extrapolated bond to sulphur from one of the adjacent atoms, and electrophiles to approach in a direction ca 20� from the perpendicular to the plane formed by the sulphur atom and its two neighbouring atoms.

Axial preference for the substituent at C-5 in 2-isopropyl-5-(CH2)nX-substituted 1,3-dioxans (X = MeS, MeSO, MeSO2, Me2S+, or OMe) is greatest when the adjacent exocyclic atom is fractionally positively charged (e.g. n= 0, X = MeSO) due to attractive interactions involving the ring oxygen atoms. The overall space requirement of the MeSO group lies between that of MeS and MeSO2.

Incidental comparisons between functional group characteristics are mentioned further in later sections of this chapter.

3 Analysis of Total Sulphur or Selenium in Organic Samples

Microdetermination of S in plant tissue using barium chloranilate, and of Se at ng levels, based on ftuorimetry of derived 4,5-benzopiazselenol or using 2,3-diaminonaphthalene as reagent, illustrate the continuing development of analytical methods.

4 Natural Occurrence of Organosulphur Compounds

Simple compounds are represented by methanethiol (Coryneform bacteria), dimethyl sulphide in beer, and di-n-propyl disulphide, which, when released from freshly cut leek leaves, stimulates egg laying by the leek moth. Besides asparagusic acid, (HSCH2)2CHCO2H, Asparagus officinalis contains 3-mer-capto- and 3-methylthio-isobutyric acid, di-2-(1-carboxypropyl) disulphide, and 3-S-acetylthio-methacrylic acid. 4-Methylthiopropylamine and (R)-3-methylsulphinylpropylamine have been isolated from Iberis amara, and further sources (fruiting bodies of Lentinus edodes) have been found for the extraordinary lentinic acid, the Nα-γ-glutamyl derivative of MeSO2(CH2SO)3- CH2CH(NH2)CO2H. Approaches to the synthesis of sparsomycin, which contains the MeSCH2SO- moiety, have been published.

Sulphur compounds must have played important roles in chemical evolution, and H2S, thiols, and sulphides were likely components of the primaeval soup.

5 Spectroscopic and Other Physical Properties of Organosulphur Compounds

Molecular Orbital Calculations. — -CND0/2 Calculations for alkyl isopropyl sulphides aimed at deducing the preferred torsion angles for the C — S — C bonds are typical of several studies with similar objectives on simple organosulphur compounds. Energetic aspects and electronic structures are also featured in these projects, the latter including an analysis of the electronic structure of sulphuranes SR4 which reveals many analogies with phosphoranes.

Ultraviolet Spectra. — Studies yielding structural information have been reported for vinyl sulphides, which have been shown to possess a lower p-π conjugation energy than vinyl ethers, and for alkali-metal arenethiolates, where the...

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