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The objective of this work was to prepare novel quinone methides to evaluate as dyestuffs with particular reference to their colour, strength and stability when dyed. An introduction to quinone methides and a brief outline of the known types is presented in Chapter 1 - with the emphasis on coloured examples. Chapter 2 describes the modification of the weakly coloured 2-phenylnaphtho[1,8-bc]furan-5-one molecule by the introduction of an auxochrome to effect a bathochromic shift into the visible region of the spectrum, and also the synthesis of the 2-arylnaphtho[l,8-bc]furan3-one and 2-phenylbenz[cd]indol-5-one chromophores. The mechanism of an unusual reaction between ethyl chloroformylacetate and 5-hydroxy-l,4-naphthoquinone (juglone) to form 3-ethoxycarbonyl6H-7-hydroxynaphtho[1,8-bc]pyran-2,6-dione is investigated in Chapter 3, whilst Chapter 4 describes the preparation of the more stable 6H-3-arylnaphtho[1,8-bc]pyran-2,6-dione and three quinodimethanes; 3,8-diphenylnaphtho(l,8-bc:4,5-b'c']dipyran-2,7-dione, 3,8-diphenylnaphtho[2,1-b:3,4-b']difuran-2,9-dione and 3,8-diphenylnaphtho(2,1-b:3,4-b']difuran-2,9-dione by condensing mandelic acid with dihydroxynaphthalenes. An improved synthesis of arylphenalenones by reacting acetophenone with 2,7-dihydroxynaphth-1-aldehyde is discussed in Chapter 5, along with the isolation and identification of 4-benzoyl (and benzyl)-2-phenyl-6H-pyrano[3a,10a-de]phenalen-6-one's, examples of a novel ring system. The visible absorption characteristics of the products are tabulated at the end of each chapter and the dyeing properties are briefly discussed.