On the basis of a preliminary u.v. assay of the dried leaf of nine species of Beilschmiedia and 26 species of Endiandra, several were selected for closer examination. Magnolol (9) was found in B.volckii and (+)-sesamin (10) was isolated from E. xanthocarpa. Endiandric acid B (2) and endiandric acid C (3) were obtained from both E. jonesii and B. tooram, and endiandric acid A (1) was found in B. obtusifolia. The new endiandric acid derivative (1′RS,3′RS,6′SR,7′SR,10′SR,11′ RS,12′RS,13′RS)-2-[6′-(3″,4″-methylenedioxyphenyl) tetracyclo [5.4.2.03,13.010,12]trideca-4′,8′-dien-11′ -yl ]acetic acid (3″,4″-methylenedioxyendiandric acid A) (4) was extracted from B. oligandra which also yielded the new phenolic benzopyran derivative (-)-(E)-2-(4′,8′-dimethylnona-3′,7′-dienyl)-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-6-ol ( oligandrol ) (12a). Several known hydrocarbon derivatives and terpenoids were isolated from the leaf of E. palmerstonii and E. baillonii, both of which were devoid of endiandric acids.

Cyclo-palladation and -platination of nitrogen donor ligands lead to insoluble p-chloro dimers which give p-bromo and p-iodo dimers on metathesis with the appropriate lithium halide. Addition of pyridine or 2,6-dimethylpyridine to the cyclopalladated dimers gives monomeric complexes with the halogen trans to the metal-carbon bond, whereas addition of 2,6-dimethylpyridine to the cycloplatinated complexes gives the isomer with the halogen cis to the metal-carbon bond. The results are discussed in terms of the mechanism of the bridge cleavage reaction.

2-(Pyridin-2'-yl) phenylmercuric acetate has been prepared by mercuration of 2-phenylpyridine. Symmetrization of the corresponding chloride by alkaline sodium stannite gave bis [2-(pyridin-2'-yl)phenyl]mercury, which was also prepared from 2-(2'-aminophenyl)pyridine by the diazo method and treatment of the initial product with copper powder and aqueous ammonia. Mercuration of benzo [h] quinoline and 3,4,5-trimethyl-1-phenylpyrazole with mercuric acetate followed by treatment with lithium chloride yielded benzo [h]quinolin-10-ylmercuric chloride and 2-(3',4',5'-trimethylpyrazol-1'-yl) phenylmercuric chloride respectively. Treatment of the former product with tribromide ions gave 10-bromobenzo[h] quinoline. The exchange Grignard reaction between 1-phenylpyrazole and ethylmagnesium bromide to give 2-(pyrazol-1'-yl) phenylmagnesium bromide has been monitored by reactions with benzonitrile and D2O to establish optimum conditions for reaction with mercuric bromide giving bis [2-(pyrazol-1'-yl)phenyl]mercury. The 199Hg n.m.r. chemical shifts of the majority of mercurials are shifted substantially downfield relative to the corresponding simple phenylmercurials consistent with weak intramolecular coordination by the heterocyclic nitrogen donor atoms, but a small upfield shift is observed for bis [2-(pyrazol-1'-yl)phenyl]mercury. The X-ray crystal structure of bis [2-(pyridin-2′-yl)phenyl]mercury [monoclinic, space group P21/n, a 12.746(2), b 11.660(2), c 5.698(1) Ǻ, β 92.81(1)′, V 845.8 Ǻ3] shows a centrosymmetric molecule with strong linear two coordination [Hg-C 2.098(8) Ǻ; C-Hg-C 180.0°] and significant but much weaker Hg-N interactions [Hg-N 2.798(7) Ǻ; N-Hg-N 180.0°] giving overall distorted square planar stereochemistry. The phenyl rings are mutually coplanar, whilst the two pyridin-2'-yl rings are parallel and inclined at 10.8° to the phenyl groups.

1,l'-Oxalylbisisatin (7) has been prepared and converted readily into a wide range of glyoxylic esters and amides (10) from which the macrocyclic metal complexes (11)-(16) have been obtained.

2,7:2,7:2,7-Linked calix [3] indoles (3a-d) have been prepared by the reaction of 4,6-dimethoxy-3-methylindole (1) and benzaldehydes with phosphoryl chloride or by a direct reaction of di (4,6-dimethoxy-3-methylindol-2-yl) phenylmethanes (2a-d) with phosphoryl chloride. An X-ray crystal structure determination of the macrocycle (3d) is reported. 4,6-Dimethoxy-3-methylindolemethanols (9) and (10) were prepared and reacted with phosphoryl chloride to study the mechanism of formation of the macrocycle.