1,3-Bis(2',2'-dicarboxyethyl)azulene (2), azulyl-1,3-bis(propanoic acid) (3), 1,3-bis(2'-carbethoxy-3'-oxo-buty1)azulene (4), 1,3-bis(3'-oxobutyl)azulene (S), diethyl azulene-l,&dipropanoate (6), and l,&bis(3'-hy-droxypropy1)azulene (7) have been synthesized via nucleophilic displacement reactions on azulyl-l,3-bis(meth~ltrimethylammonium) diiodide ( 1). Vilsmeier acylation reactions and reduction of the carbonyl groups in the 1-acylazulene products to methylenes by either the hydride reduction-alkylideneazulenium salt-hydride reduction method or, in one step, by diborane have been used to prepare I-ethylazulene, ethyl 5-(1-azulyl)-5oxopentanoate (sa), ethyl 5-( 1-azuly1)pentanoate (loa), 1-(1'-oxo-4'-carbethoxybutyl)-3-(5'-chloropentyl)azulene (1 la), azulene-1,3-bis(hexanenitrile) (14a), ethyl 4-( l-azulyl)-4-oxobutanoate (8b), 1-(4'-chlorobuty1)-3-(1'-oxo-3'-carbethoxypropyl)azulene (llb), azulene-l,3-bis(pentanenitrile) (14b), 1,3-bis(l'-oxo-3'-carbo-methoxypropy1)azulene (16), N,N-diethyl-10-( 1-azuly1)decanamide (21), pentylazulene (22), 1,3-dipentylazulene (23), 1,3-dipropionylazulene (24), and 1,3-dipropylazulene (25). The principal maxima in the visible absorption spectra for the 1-alkyl-and 1,3-dialkylazulenes are compared. The diborane reduction of the acylazulenes is discussed. A high-dilution Thorpe-Ziegler ring closure of 14a gave 1,3-(5'-cyano-6'-oxoundeca-met8hylene)azulene (26), the first example of a l13-bridged azulene. Attempts to form l,&bridged products from 14b, 21, and 6 were unsuccessful. (1965), and preceding papers.for certain cases, the reaction with aliphatic diazo compounds.' The former had provided the first step in pathways to azulene-1-ethanoic acid and azulene-lpropanoic acidP4 and the latter afforded a direct route to ethyl azulene-1-ethanoate. Since the results of an attempt to form an azulene-1,3-dialkanoic acid ester by the acid-catalyzed decomposition of an w-diazo ester in the presence of azulene were not promising, the displacement reactions of azulyl-l,3-bis(methyltrimethylammonium) diiodide (1) with the anions of active methylene compounds were tried (Scheme I). From 1 and diethyl sodiomalonate was obtained, after hydroly-

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Die Umsetzung des Ylids aus dem Phosphoniumsalz (I) mit den Carbonylverbindungen (II) in Benzol liefert die Styrylderivate (IIIa) (jeweils ein Isomeres), (IIIb),(IIIc) (jeweils cis‐ und trans‐Isomeres) bzw. (IIId) und (IIIe).

Summary: Phaeohyphomycotic cyst developed on the little finger of the right hand of a 74‐year‐old man following a burn. The diagnosis was made by histopathologic examination of the excised cyst and by isolation of the causal agent in pure culture. The excised cyst walls contained large numbers of dematiaceous, fungal elements in the form of hyphae, yeast‐like cells, toruloid hyphae, chains of catenulate cells, and some cells dividing internally by a transverse septum. The colonies of the isolate on Sabouraud dextrose agar were black to olivaceous black, smooth, shiny, and yeast‐like. Three‐week‐old colonies developed dematiaceous mycelium and conidiophores that were macronematous, branched or unbranched, septate, and smooth‐walled. The conidiogenous cells were monophialidic or, rarely, polyphialidic with very reduced collarettes that produced I‐celled conidia at their tips. When tested by the exoantigen procedure, the isolate gave positive serologic reactions to Wangiella dermatitidis. Based on these cultural and immunological characteristics, the isolate was identified as W. dermatitidis. Zusammenfassung: Eine phaeohyphomykotische Zyste entwickelte sich am kleinen Finger der rechten Hand bei einem 74jährigen Mann im Anschluß an eine Verbrennung. Die Diagnose wurde durch die histologische Untersuchung und durch die Isolierung des Erregers in Reinkultur bewiesen. Im Zystenwall fanden sich zahlreiche pigmentierte Pilzelemente als Hyphen, hefeähnliche Zellen, toruloide Hyphen, kettenartige Zellanordungen sowie mitunter als Zellen, die sich durch Ausbildung eines inneren transversen Septums teilten. Die Kolonien des isolierten Pilzes wuchsen auf Sabouraud‐Dextrose‐Agar schwarz‐ bis dunkelolivfarben, glatt, glänzend und hefeähnlich. Drei Wochen alte Kolonien entwickelten pigmentiertes Myzel und verzweigte oder unverzweigte, spetierte und glattwandige Konidiophoren. Die Konidien‐bildenden Zellen waren einreihig oder selten mehrreihig und bildeten einzellige Konidien an der Spitze. Eine serologische Testung mit Antiserum gegen Exoantigen gab positive Reaktionen auf Wangiella dermatitidis. Aufgrund der erhobenen Befunde wurde der Erreger als W. dermatitidis identifiziert.

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