J . Org. Chem., Vol. 44, No. 21, 1979 3739
Additions and Corrections Na2S04) was concentrated on a rotary evaporator, leaving 10.5 g of a colorless liquid. Analysis b y V P C (10% Zonyl E-7 on firebrick, 18 f t X ‘I4 in.) showed i t was composed of 5 6 % 1-tert-butylcyclohexene,34% 3-tert-butylcyclohexene, and 1 0 % 4-tert-butylcyclohexene. Reduction of Cumene by Calcium in MethylamineEthylenediamine ( T a b l e 11, Example 5). About 150 m L of methylamine was distilled through a KOH drying tube o n t o 10 g (0.25 g-atom) of calcium contained i n a dry, three-neck round-bottom flask equipped with a glass inlet tube, stirrer, and condenser through which ethylene glycol was circulated at -25 “C. Ethylenediamine (150 mL) and cumene (12.0 g, 100 mmol) were then added consecutively. After 24 h of stirring (internal temperature --2.5 “C), the methylamine was evaporated by disconnecting the cooling liquid from the condenser. After 1 h , solid ammonium chloride (5 g) was added and the mixture was filtered through a Buchner funnel with the aid of 50 m L of pentane. T h e filtrate was extracted with 100-mL portions of pentane and the latter was washed with 2 X 50 mL of water and then dried over molecular sieves (3A). P e n t a n e removal b y a rotary evaporator yielded 9.6 g of a colorless liquid (76%). Analysis by VPC [Carbowax 1540 capillary column (150 f t X 0.01 in.) at 80 “C] showed it was composed of 1-isopropylcyclohexene (82 % ), 3-isopropylcyclohexene (12% 1, and 4-isopropylcyclohexene (6%). It is clear from entry 5, Table 11, that reductions carried out in pure methylamine or ethylenediamine alone proceed
poorly compared to the mixed solvents. It is interesting that the reduction of naphthalene with the mixed solvent system (entry 9, Table 111) gives identical results with t h e lithium-amine procedure.6 Efforts are already underway in our laboratory to assess the effectiveness of other solvents or solvent combinations i n reductions with calcium. Likewise reductions of aromatic compounds containing functional groups are being examined. Acknowledgment. The authors a r e grateful for the financial assistance of the General Electric Foundation, which made this work possible. Registry No. C6H5C(CH,)3,98-06-6; C6H5CH(CH3)2,98-82-8; C6H5CHB,108-88-3;1-tert-butylcyclohexene,3419-66-7; 3-tert-butylcyclohexene, 14072-87-8; 4-tert-butylcyclohexene,2228-98-0; 1isopropylcyclohexene, 4292-04-0; 3-isopropylcyclohexene, 3983-08-2; 4-isopropylcyclohexene, 14072-82-3;I-methylcyclohexene, 591-49-1; 3-methylcyclohexene, 591-48-0; 4-methylcyclohexene, 591-47-9; naphthalene, 91-20-3; A9J0-octalin,493-03-8; A1~9-octalin, 1194-95-2; tetralin, 119-64-2; calcium, 7440-70-2. (6)Kaiser, E. M.; Benkeser, R. A. Org. Synth.. 1970, 50, 88
Robert A. Benkeser,* Jahyo K a n g
D e p a r t m e n t of Chemistry, P u r d u e University West Lafayette, I n d i a n a 47907 Received J u n e 5, 1979
Additions and Corrections Vol. 38, 1973
Vol. 43, 1978
Louis A. Carpino* and Grace Y. Han. The 9-Fluorenylmeth-
Peter V. Alston,* Raphael M. Ottenbrite, and Theordore Cohen. Secondary Orbital Interactions Determining Regioselectivity in the Diels-Alder Reaction. 3. Disubstituted Dienes.
oxycarbonyl Amino-Protecting Group.
Page 4218. Line 5 . For “cross-Cannizzaro reduction” read “cross-aldol alkylative cleavage”. The mechanism of this reaction was established by Burr [J. G. Burr, Jr., J . A n . Chem. SOC., 73, 823 (1951)].
”01. 42, 1977 G. J. Kent, S. A. Godleski, E. Osawa, and P. v. R. Schleyer*. Syntheses and Relative Stability of (DJ-Trishomocubane (Pentacyclo[6.3.02~6.03~10.05~9]undecane), the Pentacycloundecane Sta-
bilomer.
Page 3852. wrong
correct
wrong
correct
Page 1864. Correction to Table I. Using the coefficients in the corrected Table I, the Huckel calculations predict the preferred regioisomer for the sulfur-containing dienes. Cal Y. Meyers* and Vera M . Kolb. Facile and Selective Chlorination-Cleavage of Some Cyclanones and Cyclanols with the CC1,-KOH-t-BuOH Reagent. In Situ Conversion of Estrones and Estradiols into Dichlorodoisynolic Acids.
Page 1988. Column 1. In the first line of the equation, the structure in the bracket (the neutral vinyloxy radical) is missing the odd electron. Page 1988. Column 1. In the second line of the equation, “CCl,” should be added to the arrow at the right hand end of the line. Page 1988. Column 2. In Scheme IV, third line, the species shown as “C1-e” should be “C1-”.
4
4
9
9
Virendra Kumar and William A. Remers *. Aminoglycoside
5
5
10
10
0022-3263/79/1944-3739$01.00/0
Antibiotics. 1. Regiospecific Partial Syntheses of Ribostamycin and Butirosin B. Page 3331. Column 2. Reference 6 should read ”... Belgian Patent 845942 (Mar. 8,1977); Chem. Abstr.. 87, 202025 (1977). 0 1979 American Chemical Society
Additions and Corrections
3740 J. Org. C‘hem., Vol. 44, No. 21, 1979
Correction to Table I
Pz coeff R,
R*
R,
MOmethod
C-1
c-2
C6H5S H
CH,O CH,O
H C6H5S
Huckel Huckel
0.083 0.0
0.427 0.0
c-3 0.019 0.0
c-4
energy of HOMO, eV
0.350 0.470
Paul G. Gassman,* Ryohei Yamaguchi, and Gerald F. Koser. The Ease of Oxidation of Highly Strained Polycyclic Molecules. Page 4392. Second column, line 50. “Whereas, 18 is more easily oxidized than 17 vs. %El7 = 1.73 V; E I j zvs. SCEIs = 1.54 V), 17 was readily isomerized to 18 in the presence of silver ion.”
Page 541. Column 2, compound 6d. The data for cis-6d and trans-6d should be transposed.
Stewart W. Schneller” and Ramachandra S. Hosmane. Ring-Opening Reactions of lH-Pyrrolo[3,2-c]pyridine-4,6(5H,7H)-dione (3,7-Dideazaxanthine) and Two of Its Derivatives.
Page 873. Column 1. Structure 5 is shown with an extra double bond. I t should be: CH,C(=NOH)C(=CHPh)COOH
Page 4488. Column 1. Structure 16 is incorrectly shown as the 2-ethyl derivative. The substituent in the 2-position should be methyl, not ethyl.
Barry A. Dreikorn,* A. Frederick Elsasser, and Glen. P. Jourdan. Reaction of Thionyl Chloride with 3,4-Dihydro2(1H)-quinolinone.
Vol. 44, 1979
Page 877. Column 2. Structure 3 should be a quinoline derivative, Le., bis(2-chloro-3-quinolyl) disulfide.
Harold Kwart* and Thomas J. George. Primary Deuterium Isotope Effects in the Oxidation of Benzyl-cud Alcohol by Transition Elements and Related Reagents: Mechanisms of Electron Transfer. Page 163. Right column. The sentence directly below the orbital diagram 6 should read: “... 6 is intended to illustrate the structure in which nonlinear transfer of hydrogen can take place.” D. Soerens, J. Sandrin, F. Ungemach, P. Mokry, G. S. Wu, E. Yamanaka, L.Hutchins, M. DiPierro, and J. M. Cook*. Study of the Pictet-Spengler Reaction in Aprotic Media: Synthesis of the (3-G.alactosidase Inhibitor, Pyridinolol.
Augustine Silveira, Jr.* and Shantilal K. Satra. Study of the Ring Opening Reactions of 4-Bromo-3,4-disubstituted-2isoxazolin-5-ones with Aqueous Sodium Hydroxide.
Howard E. Smith,* Benjamin G. Padilla, Jon R. Neergaard, and Fu-Ming Chen. Optically Active Amines. 26. Spectral Observations on Chiral Schiff Bases. Page 1694. Column 1, Experimental Section. The heading of paragraph 4 should be (R)-N-Benzylidene-a-benzylethylamine
[ ( R)-sal.
Page 1694. Column 1, Experimental Section. The head of paragraph 5 should be ( R ) - N - o-Methoxybenzy1idene)-a( benzylethylamine [ (R)-8b)].
